Pesticidal compositions and methods

ABSTRACT

This disclosure relates to the field of molecules having pesticidal utility against pests in phyla Nematoda, Arthropoda, and/or Mollusca, processes to produce such molecules and intermediates used in such processes, compositions containing such molecules, and processes of using such molecules against such pests. These molecules may be used, for example, as nematicides, acaricides, insecticides, miticides, and/or molluscicides. This document discloses molecules having the structure of Formula A.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional PatentApplication Ser. No. 62/784,911 filed Dec. 26, 2018, which is expresslyincorporated by reference herein.

FIELD OF THE INVENTION

The invention disclosed in this document is related to the field ofpesticides and their use in controlling pests.

BACKGROUND OF THE INVENTION

Pests cause millions of human deaths around the world each year.Furthermore, there are more than ten thousand species of pests thatcause losses in agriculture. These agricultural losses amount tobillions of U.S. dollars each year. Termites cause damage to variousstructures such as homes. These termite damage losses amount to billionsof U.S. dollars each year. As a final note, many stored food pests eatand adulterate stored food. These stored food losses amount to billionsof U.S. dollars each year, but more importantly, deprive people ofneeded food.

There is an acute need for new pesticides. Insects are developingresistance to pesticides in current use. Hundreds of insect species areresistant to one or more pesticides.

The development of resistance to some of the older pesticides, such asDDT, the carbamates, and the organophosphates, is well known. Butresistance has even developed to some of the newer pesticides.Therefore, a need exists for new pesticides and particularly forpesticides that have new modes of action.

SUMMARY OF THE INVENTION

In one aspect, provided are molecules having the structure of Formula A:

wherein:(A) Ar¹ is selected from

(1) furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, thienyl, or

(2) substituted furanyl, substituted phenyl, substituted pyridazinyl,substituted pyridyl, substituted pyrimidinyl, or substituted thienyl,

-   -   wherein said substituted furanyl, substituted phenyl,        substituted pyridazinyl, substituted pyridyl, substituted        pyrimidinyl, and substituted thienyl have one or more        substituents independently selected from H, F, Cl, Br, I, CN,        OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈        haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈        haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈        haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),        C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈        alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈        alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl),        (C₁-C₈ alkyl)OC(═O)O(C₁₋₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁₋₈        alkyl), (C₁-C₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁₋₈        alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl,        phenoxy, Si(C₁-C₈ alkyl)₃, or S(═O)_(n)NR^(x)R^(y), or (Het-1),    -   wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl,        alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl, alkynyl,        phenyl, phenoxy, and (Het-1) substituent may be optionally        substituted with one or more substituents independently selected        from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y),        C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈        alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl,        C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),        C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈        cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈        alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)(C₁-C₈ alkyl), (C₁-C₈        alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),        C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)OC₁-C₈        alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl,        (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃,        S(═O)_(n)NR^(x)R^(y), or (Het-1);        (B) Het is a 5- or 6-membered, saturated or unsaturated,        heterocyclic ring, containing one or more heteroatoms        independently selected from nitrogen, sulfur, or oxygen, and        where Ar¹ and Ar² are not ortho to each other (but may be meta        or para, such as, for a five-membered ring they are 1,3 and for        a 6-membered ring they are either 1,3 or 1,4) and where said        heterocyclic ring may also be substituted with one or more        substituents independently selected from H, F, Cl, Br, I, CN,        OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈        haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈        haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),        C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈        cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈        alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁₋₈ alkyl), (C₁-C₈        alkyl)OC(═O)(C₁₋₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),        C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈        alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl,        (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃, or        S(═O)_(n)NR^(x)R^(y),

wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxy,haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl, alkynyl, phenyl, andphenoxy substituent may be optionally substituted with one or moresubstituents independently selected from H, F, Cl, Br, I, CN, OH, SH,NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈alkyl)₃, or S(═O)_(n)NR^(x)R^(y);

(C) Ar² is selected from

(1) furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, thienyl, or

(2) substituted furanyl, substituted phenyl, substituted pyridazinyl,substituted pyridyl, substituted pyrimidinyl, or substituted thienyl,

-   -   wherein said substituted furanyl, substituted phenyl,        substituted pyridazinyl, substituted pyridyl, substituted        pyrimidinyl, and substituted thienyl, have one or more        substituents independently selected from H, F, Cl, Br, I, CN,        OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈        haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈        haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),        C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈        cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈        alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl),        (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁₋₈        alkyl), C(═O)(C₁₋₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈        alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁₋₈ alkyl), (C₁-C₈        alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈        alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1),    -   wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl,        alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl, alkynyl,        phenyl, phenoxy, and (Het-1) substituent may be optionally        substituted with one or more substituents independently selected        from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y),        C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈        alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl,        C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),        C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈        cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈        alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl),        (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈        alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈        alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),        (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy,        Si(C₁-C₈ alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1);        (D) L is linker selected from

(1) a bond,

(2) —CR⁴R⁵—CR⁶R⁷—, or

(3) —CR⁴═CR⁶—,

wherein each of R⁴, R⁵, R⁶, and R⁷ is selected from H, F, Cl, Br, I, CN,OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl,C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈alkynyl, C₂-C₈ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C(═O)(C₁-C₆ alkyl), C(═O)O(C₁-C₆ alkyl), C(═O)(C₃-C₆cycloalkyl), C(═O)O(C₃-C₆ cycloalkyl), C(═O)(C₂-C₆ alkenyl),C(═O)O(C₂-C₆ alkenyl), (C₁-C₆ alkyl)O(C₁-C₆ alkyl), (C₁-C₆alkyl)S(═O)_(n)(C₁-C₆ alkyl), C(═O)(C₁-C₆ alkyl)C(═O)O(C₁-C₆ alkyl),S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₁-C₈haloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), phenyl, or phenoxy;

(E) R⁴ and R⁶ together can optionally form a 3- to 7-membered saturatedor unsaturated ring which may contain C═O, C═S, N, S or O, and isoptionally substituted with H, OH, F, Cl, Br, I, CN, NO₂, NR_(x)R_(y),C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ hydroxyalkyl, C₃-C₆ cycloalkyl,C₃-C₆ halocycloalkyl, C₃-C₆ hydroxycycloalkyl, C₃-C₆ cycloalkoxy, C₃-C₆halocycloalkoxy, C₃-C₆ hydroxycycloalkoxy, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, C₂-C₆ alkenyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkynyl, S(═O)_(n)(C₁-C₆ alkyl), S(═O)_(n)(C₁-C₆ haloalkyl),OSO₂(C₁-C₆ alkyl), OSO₂(C₁-C₆ haloalkyl), C(═O)H, C(═O)OH,C(═O)NR_(x)R_(y), (C₁-C₆ alkyl)NR_(x)R_(y), C(═O)(C₁-C₆ alkyl),C(═O)O(C₁-C₆ alkyl), C(═O)(C₁-C₆ haloalkyl), C(═O)O(C₁-C₆ haloalkyl),C(═O)(C₃-C₆ cycloalkyl), C(═O)O(C₃-C₆ cycloalkyl), C(═O)(C₂-C₆ alkenyl),C(═O)O(C₂-C₆ alkenyl), (C₁-C₆ alkyl)O(C₁-C₆ alkyl), (C₁-C₆alkyl)S(═O)_(n)(C₁-C₆ alkyl), C(═O)(C₁-C₆ alkyl)C(═O)O(C₁-C₆ alkyl),phenyl, phenoxy, and Het-1;(F) Q¹ is selected from O or S;(G) Q² is selected from O or S;(H) R¹ is selected from (J), H, C₁-C₈ alkyl, C₃-C₈ cycloalkyl, C₂-C₈alkenyl, C₂-C₈ alkynyl, C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, C(═O)(Het-1), (Het-1), (C₁-C₈ alkyl)-(Het-1), (C₁-C₈alkyl)-C(═O)—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-O—C(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-O—C(═O)NR^(x)R^(y), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)(Het-1),(C₁-C₈ alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)OH, (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(x))(R^(y)), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)(N(R^(y))C(═O)O—(C₁-C₈ alkyl)C(═O)OH,(C₁-C₈ alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)—(C₃-C₈ cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈alkyl)-OC(═O)—(C₁-C₈ alkyl)N(R^(x))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-NR^(x)R^(y), (C₁-C₈ alkyl)-S-(Het-1), (C₁-C₈alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1),

wherein each alkyl, cycloalkyl, phenyl, and (Het-1) are optionallysubstituted with one or more substituents independently selected from H,F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl,C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy,C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl,S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl),S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl),OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)OH, C(═O)NR^(x)R^(y), (C₁-C₈alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl),(C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃,S(═O)_(n)NR^(x)R^(y), or (Het-1);

(I) R² is selected from (J), H, OH, SH, C₁-C₈ alkyl, C₁-C₈ haloalkyl,C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynylS(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)H, C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁₋₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,C(═O)(Het-1), (Het-1), (C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)—(C₁-C₈alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-O—C(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-O—C(═O)NR^(x)R^(y), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)(Het-1),(C₁-C₈ alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)OH, (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(x))(R^(y)), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)(N(R^(y))C(═O)O—(C₁-C₈ alkyl)C(═O)OH,(C₁-C₈ alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)—(C₃-C₈ cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈alkyl)-OC(═O)—(C₁-C₈ alkyl)N(R^(x))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-NR^(x)R^(y), (C₁-C₈ alkyl)-S-(Het-1), (C₁-C₈alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1),

wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkoxy,halocycloalkoxy, alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl,alkynyl, phenyl, and (Het-1), are optionally substituted with one ormore substituents independently selected from H, F, Cl, Br, I, CN, OH,SH, NO₂, oxo, thioxo, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)OH, C(═O)(C₁-C₈alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁₋₈haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl),C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁₋₈ alkyl),(C₁-C₈ alkyl)S(═O)_(n)(C₁₋₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, halophenyl,phenoxy, and (Het-1);

(J) R¹ and R² may be a 1- to 4-membered saturated or unsaturated,hydrocarbyl link, which may contain one or more heteroatoms selectedfrom nitrogen, sulfur, and oxygen, and together with (Q²)(C)(N) forms a4- to 7-membered cyclic structure, wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo,NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl,C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, substituted phenyl,phenoxy, or (Het-1);(K) R³ is selected from C₃-C₈ cycloalkyl, phenyl, (C₁-C₈ alkyl)phenyl,(C₁-C₈ alkyl)-O-phenyl, (C₂-C₈ alkenyl)-O-phenyl, (Het-1), (C₁-C₈alkyl)-(Het-1), (C₁-C₈ alkyl)-O-(Het-1),

wherein the C₃-C₈ cycloalkyl, phenyl, (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, (C₂-C₈ alkenyl)-O-phenyl, (Het-1), (C₁-C₈alkyl)-(Het-1), or (C₁-C₈ alkyl)-O-(Het-1) may be optionally substitutedwith one or more substituents independently selected from H, F, Cl, Br,I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy,C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl,C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ haloalkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈alkyl)₃, S(═O)_(n)NR^(x)R^(y), (Het-1), or wherein two adjacentsubstituents form a 5- or 6-membered saturated or unsaturated,hydrocarbyl link, which may contain one or more heteroatoms selectedfrom nitrogen, sulfur, and oxygen, and wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo;

(L) R^(x) and R^(y) are independently selected from H, OH, SH, C₁-C₈alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy,C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl,S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl),S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl),OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl),C(═O)(C₁₋₈ haloalkyl), C(═O)O(C₁₋₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl),(C₁-C₈ alkyl)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁₋₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,C(═O)(Het-1), (Het-1), (C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)—(C₁-C₈alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-O—C(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-C(═O)(Het-1), (C₁-C₈alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)O—(C₁-C₈alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₃-C₈cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈ alkyl)-S-(Het-1),(C₁-C₈ alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1),

wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkoxy,halocycloalkoxy, alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl,alkynyl, phenyl, and (Het-1), are optionally substituted with one ormore substituents independently selected from H, F, Cl, Br, I, CN, OH,SH, NO₂, oxo, thioxo, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)OH, C(═O)(C₁-C₈alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl),C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, halophenyl, phenoxy, and (Het-1),

or R^(x) and R^(y) together can optionally form a 5- to 7-memberedsaturated or unsaturated cyclic group which may contain one or moreheteroatoms selected from nitrogen, sulfur, and oxygen, and where saidcyclic group may be substituted with H, F, Cl, Br, I, CN, OH, SH, NO₂,oxo, thioxo, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl,C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, substituted phenyl,phenoxy, and (Het-1);

(M) (Het-1) is a 5- or 6-membered, saturated or unsaturated,heterocyclic ring, containing one or more heteroatoms independentlyselected from nitrogen, sulfur or oxygen, wherein said heterocyclic ringmay also be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo,NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl,C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl),(C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ haloalkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁₋₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, and phenoxy,

wherein each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl, andphenoxy may be optionally substituted with one or more substituentsindependently selected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo,thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)NR^(x)R^(y),(C₁-C₈ alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, and phenoxy; and

(N) n is each individually 0, 1, or 2.

In some embodiments, the molecules provided have the structure ofFormula One, Formula Two, or Formula Three:

wherein:(A) Ar¹ is a phenyl or substituted phenyl having one or moresubstituents independently selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₁-C₆ alkoxy and C₁-C₆ haloalkoxy;(B) Het is triazolyl;(C) Ar² is a phenyl or a substituted phenyl having one or moresubstituents independently selected from H, F, Cl, Br, I, CN, NO₂,NR^(x)R^(y), OH, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, and C₁-C₆haloalkoxy;(D1) Each R⁴ and R⁶ is selected from (E), H, F, Cl, Br, I, CN, oxo,C₁-C₆ alkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆cycloalkenyl, C₃-C₆ halocycloalkyl, and phenyl;(D2) Each R⁵ and R⁷ is selected from, H, F, Cl, Br, I, CN, oxo, C₁-C₆alkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl,C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkenyl,C₃-C₆ halocycloalkyl, and phenyl;(E) R⁴ and R⁶ together can optionally form a 3- to 7-membered saturatedor unsaturated ring which may contain C═O, C═S, N, S or O, and isoptionally substituted with H, OH, F, Cl, Br, I, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, phenyl, phenoxy, and Het-1;

(F) Q¹ is O; (G) Q² is S;

(H) R¹ is selected from (J), H, C₁-C₆ alkyl or C₂-C₆ alkenyl, whereinsaid alkyl or alkenyl is optionally substituted with a C₃-C₆ cycloalkylor C₁-C₆ alkoxy;(F) R² is selected from (J), H, OH, C₁-C₆ alkyl or C₂-C₆ alkenyl,wherein said alkyl or alkenyl is optionally substituted with a C₃-C₆cycloalkyl or C₁-C₆ alkoxy;(G) R³ is phenyl or (Het-1), wherein the phenyl or (Het-1) may beoptionally substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₁-C₆ alkoxy,C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl,S(═O)_(n)(C₁-C₆ alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), (C₁-C₆ alkyl)O(C₁-C₆alkyl), (C₁-C₆ alkyl)O(C₁-C₆ haloalkyl), (C₁-C₆ alkyl)S(═O)_(n)(C₁-C₆alkyl), phenyl, and oxo or wherein two adjacent substituents form a 5-or 6-membered saturated or unsaturated, hydrocarbyl link, which maycontain one or more heteroatoms selected from nitrogen, sulfur, andoxygen, and such ring is optionally substituted with one or moresubstituents selected from H, F, Cl, Br, I, CN, OH, SH, NO₂,NR^(x)R^(y), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, S(═O)_(n)(C₁-C₆ alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl,and oxo;(H) R^(x) and R^(y) are independently selected from H, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, and phenyl;(I) (Het-1) is a 5- or 6-membered, saturated or unsaturated,heterocyclic ring, containing one or more heteroatoms independentlyselected from nitrogen, sulfur or oxygen, wherein said heterocyclic ringmay also be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ haloalkyl), S(═O)_(n)(C₁-C₆alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo; and(J) R¹ and R² may be a 1- to 4-membered saturated or unsaturated,hydrocarbyl link, which may contain one or more heteroatoms selectedfrom nitrogen, sulfur, and oxygen, and together with (Q²)(C)(N) forms a4- to 7-membered cyclic structure, wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo.

In one embodiment, Ar¹ is substituted phenyl having one or moresubstituents independently selected from OCF₃, OCF₂CF₃, and CF₃. Inanother embodiment, Het is 1,2,4-triazolyl. In another embodiment, Ar²is phenyl.

In another embodiment, R¹ and R² together form a 5-membered saturated orunsaturated ring containing one or two C═O, and such ring is optionallysubstituted with H, OH, F, Cl, Br, I, CN, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, phenyl or phenoxy. In anotherembodiment, R³ is substituted phenyl with one or more substituentsindependently selected from H, OH, F, Cl, Br, I, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, (C₁-C₆ alkyl)O(C₁-C₆alkyl), (C₁-C₆ alkyl)O(C₁-C₆ haloalkyl), (C₁-C₆ alkyl)S(═O)_(n)(C₁-C₆alkyl), C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy. In another embodiment, R³ is substituted phenyl wherein twoadjacent substituents form a 5- or 6-membered saturated or unsaturated,hydrocarbyl link, which may contain one or more heteroatoms selectedfrom nitrogen, sulfur, and oxygen, and wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo.

In another aspect, provided is a process to apply a molecule providedherein. The process comprises applying a molecule provided herein, to anarea to control a pest, in an amount sufficient to control such pest. Inone embodiment, the pest is beet armyworm (BAW), cabbage looper (CL), orgreen peach aphid (GPA).

In another aspect, provided is a molecule that is a pesticidallyacceptable acid addition salt, a salt derivative, a solvate, or an esterderivative, of a molecule provided herein. In another aspect, providedis a molecule provided herein wherein at least one H is ²H or at leastone C is ¹⁴C. In another aspect, provided is a composition comprising amolecule provided herein and at least one other compound havinginsecticidal, herbicidal, acaricidal, nematicidal, or fungicidalactivity. In another aspect, provided is a composition comprising amolecule provided herein and a seed.

In another aspect, provided is a process comprising applying a moleculeprovided herein to a genetically modified plant or agenetically-modified seed, which has been genetically modified toexpress one or more specialized traits. In another aspect, provided is aprocess comprising: orally administering or topically applying amolecule provided herein, to a non-human animal, to controlendoparasites, ectoparasites, or both.

DETAILED DESCRIPTION OF THE INVENTION

The examples given for the substituents are (except for halo)non-exhaustive and must not be construed as limiting the inventiondisclosed in this document.

Definitions

“Alkenyl” means an acyclic, unsaturated (at least one carbon-carbondouble bond), branched or unbranched, substituent consisting of carbonand hydrogen, for example, vinyl, allyl, butenyl, pentenyl, hexenyl,heptenyl, octenyl, nonenyl, and decenyl.

“Alkenyloxy” means an alkenyl further consisting of a carbon-oxygensingle bond, for example, allyloxy, butenyloxy, pentenyloxy, hexenyloxy,heptenyloxy, octenyloxy, nonenyloxy, and decenyloxy.

“Alkoxy” means an alkyl further consisting of a carbon-oxygen singlebond, for example, methoxy, ethoxy, propoxy, isopropoxy, 1-butoxy,2-butoxy, isobutoxy, tert-butoxy, pentoxy, 2-methylbutoxy,1,1-dimethylpropoxy, hexoxy, heptoxy, octoxy, nonoxy, and decoxy.

“Alkyl” means an acyclic, saturated, branched or unbranched, substituentconsisting of carbon and hydrogen, for example, methyl, ethyl, propyl,isopropyl, 1-butyl, 2-butyl, isobutyl, tert-butyl, pentyl,2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl, octyl, nonyl, anddecyl.

“Alkynyl” means an acyclic, unsaturated (at least one carbon-carbontriple bond, and any double bonds), branched or unbranched, substituentconsisting of carbon and hydrogen, for example, ethynyl, propargyl,butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, and decynyl.

“Alkynyloxy” means an alkynyl further consisting of a carbon-oxygensingle bond, for example, pentynyloxy, hexynyloxy, heptynyloxy,octynyloxy, nonynyloxy, and decynyloxy.

“Aryl” means a cyclic, aromatic substituent consisting of hydrogen andcarbon, for example, phenyl, naphthyl, and biphenyl.

“Cycloalkenyl” means a monocyclic or polycyclic, unsaturated (at leastone carbon-carbon double bond) substituent consisting of carbon andhydrogen, for example, cyclobutenyl, cyclopentenyl, cyclohexenyl,cycloheptenyl, cyclooctenyl, cyclodecenyl, norbornenyl,bicyclo[2.2.2]octenyl, tetrahydronaphthyl, hexahydronaphthyl, andoctahydronaphthyl.

“Cycloalkenyloxy” means a cycloalkenyl further consisting of acarbon-oxygen single bond, for example, cyclobutenyloxy,cyclopentenyloxy, cyclohexenyloxy, cycloheptenyloxy, cyclooctenyloxy,cyclodecenyloxy, norbornenyloxy, and bicyclo[2.2.2]octenyloxy.

“Cycloalkyl” means a monocyclic or polycyclic, saturated substituentconsisting of carbon and hydrogen, for example, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, norbornyl,bicyclo[2.2.2]octyl, and decahydronaphthyl.

“Cycloalkoxy” means a cycloalkyl further consisting of a carbon-oxygensingle bond, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclodecyloxy,norbornyloxy, and bicyclo[2.2.2]octyloxy.

“Halo” means fluoro, chloro, bromo, and iodo.

“Haloalkyl” means an alkyl further consisting of, from one to themaximum possible number of, identical or different, halos, for example,fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoromethyl,2-fluoroethyl, 2,2,2-trifluoroethyl, chloromethyl, trichloromethyl, and1,1,2,2-tetrafluoroethyl.

“Heterocyclyl” means a cyclic substituent that may be fully saturated,partially unsaturated, or fully unsaturated, where the cyclic structurecontains at least one carbon and at least one heteroatom, where saidheteroatom is nitrogen, sulfur, or oxygen, for example, benzofuranyl,benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzothienyl,benzothiazolyl cinnolinyl, furanyl, indazolyl, indolyl, imidazolyl,isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, 1,3,4-oxadiazolyl,oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl,pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl,quinoxalinyl, 1,2,3,4-tetrazolyl, thiazolinyl, thiazolyl, thienyl,1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3-triazolyl, and1,2,4-triazolyl.

Compounds

The compounds of this invention have the structure of Formula A:

wherein:(A) Ar¹ is selected from

(1) furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, thienyl, or

(2) substituted furanyl, substituted phenyl, substituted pyridazinyl,substituted pyridyl, substituted pyrimidinyl, or substituted thienyl,

-   -   wherein said substituted furanyl, substituted phenyl,        substituted pyridazinyl, substituted pyridyl, substituted        pyrimidinyl, and substituted thienyl have one or more        substituents independently selected from H, F, Cl, Br, I, CN,        OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈        haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈        haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈        haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),        C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈        alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈        alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl),        (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁₋₈        alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈        alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈        alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃, or        S(═O)_(n)NR^(x)R^(y), or (Het-1),    -   wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl,        alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl, alkynyl,        phenyl, phenoxy, and (Het-1) substituent may be optionally        substituted with one or more substituents independently selected        from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y),        C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈        alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl,        C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁₋₈ haloalkyl),        C(═O)O(C₁₋₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈        cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈        alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl),        (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈        alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈        alkyl)C(═O)OC₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),        (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy,        Si(C₁-C₈ alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1);        (B) Het is a 5- or 6-membered, saturated or unsaturated,        heterocyclic ring, containing one or more heteroatoms        independently selected from nitrogen, sulfur, or oxygen, and        where Ar¹ and Ar² are not ortho to each other (but may be meta        or para, such as, for a five-membered ring they are 1,3 and for        a 6-membered ring they are either 1,3 or 1,4) and where said        heterocyclic ring may also be substituted with one or more        substituents independently selected from H, F, Cl, Br, I, CN,        OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈        haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈        haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),        C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈        cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈        alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁₋₈ alkyl), (C₁-C₈        alkyl)OC(═O)(C₁₋₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),        C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈        alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl,        (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃, or        S(═O)_(n)NR^(x)R^(y),

wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxy,haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl, alkynyl, phenyl, andphenoxy substituent may be optionally substituted with one or moresubstituents independently selected from H, F, Cl, Br, I, CN, OH, SH,NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈alkyl)₃, or S(═O)_(n)NR^(x)R^(y);

(C) Ar² is selected from

(1) furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, thienyl, or

(2) substituted furanyl, substituted phenyl, substituted pyridazinyl,substituted pyridyl, substituted pyrimidinyl, or substituted thienyl,

-   -   wherein said substituted furanyl, substituted phenyl,        substituted pyridazinyl, substituted pyridyl, substituted        pyrimidinyl, and substituted thienyl, have one or more        substituents independently selected from H, F, Cl, Br, I, CN,        OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈        haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈        haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),        C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈        cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈        alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl),        (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁₋₈        alkyl), C(═O)(C₁₋₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈        alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁₋₈ alkyl), (C₁-C₈        alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈        alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1),    -   wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl,        alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl, alkynyl,        phenyl, phenoxy, and (Het-1) substituent may be optionally        substituted with one or more substituents independently selected        from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y),        C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈        alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl,        C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl),        S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),        S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈        haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),        C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),        C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈        cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈        alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)(C₁-C₈ alkyl), (C₁-C₈        alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),        C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈        alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl,        (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃,        S(═O)_(n)NR^(x)R^(y), or (Het-1);        (D) L is linker selected from

(1) a bond,

(2) —CR⁴R⁵—CR⁶R⁷—, or

(3) —CR⁴═CR⁶—,

wherein each of R⁴, R⁵, R⁶, and R⁷ is selected from H, F, Cl, Br, I, CN,OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl,C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈alkynyl, C₂-C₈ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C(═O)(C₁-C₆ alkyl), C(═O)O(C₁-C₆ alkyl), C(═O)(C₃-C₆cycloalkyl), C(═O)O(C₃-C₆ cycloalkyl), C(═O)(C₂-C₆ alkenyl),C(═O)O(C₂-C₆ alkenyl), (C₁-C₆ alkyl)O(C₁-C₆ alkyl), (C₁-C₆alkyl)S(═O)_(n)(C₁-C₆ alkyl), C(═O)(C₁-C₆ alkyl)C(═O)O(C₁-C₆ alkyl),S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₁-C₈haloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), phenyl, or phenoxy;

(E) R⁴ and R⁶ together can optionally form a 3- to 7-membered ring whichmay contain C═O, C═S, N, S or O, and is optionally substituted with OH,F, Cl, Br, I, CN, NO₂, NR_(x)R_(y), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆hydroxyalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₃-C₆hydroxycycloalkyl, C₃-C₆ cycloalkoxy, C₃-C₆ halocycloalkoxy, C₃-C₆hydroxycycloalkoxy, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆ alkenyl, C₃-C₆cycloalkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkynyl, S(═O)_(n)(C₁-C₆ alkyl),S(═O)_(n)(C₁-C₆ haloalkyl), OSO₂(C₁-C₆ alkyl), OSO₂(C₁-C₆ haloalkyl),C(═O)H, C(═O)OH, C(═O)NR^(x)R^(y), (C₁-C₆ alkyl)NR_(x)R_(y), C(═O)(C₁-C₆alkyl), C(═O)O(C₁-C₆ alkyl), C(═O)(C₁-C₆ haloalkyl), C(═O)O(C₁-C₆haloalkyl), C(═O)(C₃-C₆ cycloalkyl), C(═O)O(C₃-C₆ cycloalkyl),C(═O)(C₂-C₆ alkenyl), C(═O)O(C₂-C₆ alkenyl), (C₁-C₆ alkyl)O(C₁-C₆alkyl), (C₁-C₆ alkyl)S(═O)_(n)(C₁-C₆ alkyl), C(═O)(C₁-C₆alkyl)C(═O)O(C₁-C₆ alkyl), phenyl, phenoxy, and Het-1;(F) Q¹ is selected from O or S;(G) Q² is selected from O or S;(H) R¹ is selected from (J), H, C₁-C₈ alkyl, C₃-C₈ cycloalkyl, C₂-C₈alkenyl, C₂-C₈ alkynyl, C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, C(═O)(Het-1), (Het-1), (C₁-C₈ alkyl)-(Het-1), (C₁-C₈alkyl)-C(═O)—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-O—C(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-O—C(═O)NR^(x)R^(y), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)(Het-1),(C₁-C₈ alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)OH, (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(x))(R^(y)), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)(N(R^(y))C(═O)O—(C₁-C₈ alkyl)C(═O)OH,(C₁-C₈ alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)—(C₃-C₈ cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈alkyl)-OC(═O)—(C₁-C₈ alkyl)N(R^(x))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-NR^(x)R^(y), (C₁-C₈ alkyl)-S-(Het-1), (C₁-C₈alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1),

wherein each alkyl, cycloalkyl, phenyl, and (Het-1) are optionallysubstituted with one or more substituents independently selected from H,F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl,C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy,C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl,S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl),S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl),OSO₂(C₁₋₈ haloalkyl), C(═O)H, C(═O)OH, C(═O)NR^(x)R^(y), (C₁-C₈alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl),(C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃,S(═O)_(n)NR^(x)R^(y), or (Het-1);

(I) R² is selected from (J), H, OH, SH, C₁-C₈ alkyl, C₁-C₈ haloalkyl,C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)H, C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,C(═O)(Het-1), (Het-1), (C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)—(C₁-C₈alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-O—C(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-O—C(═O)NR^(x)R^(y), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)(Het-1),(C₁-C₈ alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)OH, (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(x))(R^(y)), (C₁-C₈alkyl)-C(═O)N(R^(y))(C₁-C₈ alkyl)N(R^(y))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)(N(R^(y))C(═O)O—(C₁-C₈ alkyl)C(═O)OH,(C₁-C₈ alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)—(C₃-C₈ cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈alkyl)-OC(═O)—(C₁-C₈ alkyl)N(R^(x))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-NR^(x)R^(y), (C₁-C₈ alkyl)-S-(Het-1), (C₁-C₈alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1),

wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkoxy,halocycloalkoxy, alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl,alkynyl, phenyl, and (Het-1), are optionally substituted with one ormore substituents independently selected from H, F, Cl, Br, I, CN, OH,SH, NO₂, oxo, thioxo, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)OH, C(═O)(C₁-C₈alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁₋₈haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl),C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, halophenyl, phenoxy, and (Het-1);

(J) R¹ and R² may be a 1- to 4-membered saturated or unsaturated,hydrocarbyl link, which may contain one or more heteroatoms selectedfrom nitrogen, sulfur, and oxygen, and together with (Q²)(C)(N) forms a4- to 7-membered cyclic structure, wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo,NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl,C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, substituted phenyl,phenoxy, or (Het-1);(K) R³ is selected from C₃-C₈ cycloalkyl, phenyl, (C₁-C₈ alkyl)phenyl,(C₁-C₈ alkyl)-O-phenyl, (C₂-C₈ alkenyl)-O-phenyl, (Het-1), (C₁-C₈alkyl)-(Het-1), (C₁-C₈ alkyl)-O-(Het-1),

wherein the C₃-C₈ cycloalkyl, phenyl, (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, (C₂-C₈ alkenyl)-O-phenyl, (Het-1), (C₁-C₈alkyl)-(Het-1), or (C₁-C₈ alkyl)-O-(Het-1) may be optionally substitutedwith one or more substituents independently selected from H, F, Cl, Br,I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy,C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl,C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ haloalkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1) or wherein two adjacentsubstituents form a 5- or 6-membered saturated or unsaturated,hydrocarbyl link, which may contain one or more heteroatoms selectedfrom nitrogen, sulfur, and oxygen, and wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo;

(L) R^(x) and R^(y) are independently selected from H, OH, SH, C₁-C₈alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy,C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl,S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl),S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl),OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁₋₈ alkyl), (C₁-C₈alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, (C₁-C₈ alkyl)phenyl,(C₁-C₈ alkyl)-O-phenyl, C(═O)(Het-1), (Het-1), (C₁-C₈ alkyl)-(Het-1),(C₁-C₈ alkyl)-C(═O)—(C₁₋₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl),(C₁-C₈ alkyl)-O—C(═O)O—(C₁₋₈ alkyl), (C₁-C₈ alkyl)-C(═O)(Het-1), (C₁-C₈alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)O—(C₁-C₈alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₃-C₈cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈ alkyl)-S-(Het-1),(C₁-C₈ alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1),

wherein each alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkoxy,halocycloalkoxy, alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl,alkynyl, phenyl, and (Het-1), are optionally substituted with one ormore substituents independently selected from H, F, Cl, Br, I, CN, OH,SH, NO₂, oxo, thioxo, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)OH, C(═O)(C₁-C₈alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl),C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, halophenyl, phenoxy, and (Het-1),

or R^(x) and R^(y) together can optionally form a 5- to 7-memberedsaturated or unsaturated cyclic group which may contain one or moreheteroatoms selected from nitrogen, sulfur, and oxygen, and where saidcyclic group may be substituted with H, F, Cl, Br, I, CN, OH, SH, NO₂,oxo, thioxo, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl,C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, substituted phenyl,phenoxy, and (Het-1);

(M) (Het-1) is a 5- or 6-membered, saturated or unsaturated,heterocyclic ring, containing one or more heteroatoms independentlyselected from nitrogen, sulfur or oxygen, wherein said heterocyclic ringmay also be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo,NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy,C₁₋₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl,C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl),(C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ haloalkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁₋₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, and phenoxy,

wherein each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl, andphenoxy may be optionally substituted with one or more substituentsindependently selected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo,thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)NR^(x)R^(y),(C₁-C₈ alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, and phenoxy; and

(N) n is each individually 0, 1, or 2.

In one embodiment, Ar¹ is phenyl or substituted phenyl having one ormore substituents independently selected from C₁-C₆ alkyl, C₁-C₆haloalkyl, and C₁-C₆ haloalkoxy.

In another embodiment, Het is a triazolyl, imidazolyl, pyrrolyl, orpyrazolyl.

In another embodiment, Ar² is phenyl or a substituted phenyl having oneor more substituents independently selected from C₁-C₆ alkyl, C₁-C₆haloalkyl, and C₁-C₆ haloalkoxy.

In another embodiment, R¹ and R² are independently selected from H,C₁-C₆ alkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy, phenyl, orphenoxy;

wherein R¹ and R² together can optionally form a 5- to 7-membered ringand is optionally substituted with OH, F, Cl, Br, I, CN, NO₂, C₁-C₆alkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy, phenyl, phenoxy,or (Het-1),

wherein (Het-1) is a 5- or 6-membered, saturated or unsaturated,heterocyclic ring, containing one or more heteroatoms independentlyselected from nitrogen, sulfur and oxygen.

In another embodiment, R¹ and R² together form a 5- to 7-membered ringcontaining one or more C═O, C═S, N, S or O, and such ring is optionallysubstituted with H, OH, F, Cl, Br, I, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, phenyl, or phenoxy,

wherein said phenyl or phenoxy is optionally substituted with one ormore H, OH, F, Cl, Br, I, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy,C₁-C₆ haloalkoxy, or phenyl.

In another embodiment, R¹ and R² together form a 5- to 7-membered ringwhich contains one or more C═O, C═S, N, S or O.

In another embodiment, R³ is phenyl optionally substituted with one ormore substituents independently selected from H, OH, F, Cl, Br, I, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₁-C₆ alkenyl, C₁-C₆ haloalkenyl, C₃-C₆ cycloalkyl,C₃-C₆ halocycloalkyl, NR^(x)R^(y), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)O(C₁-C₈ haloalkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), phenyl,or phenoxy. In another embodiment, R³ is phenyl optionally substitutedwherein two adjacent substituents form a 5- or 6-membered saturated orunsaturated, hydrocarbyl link, which may contain one or more heteroatomsselected from nitrogen, sulfur, and oxygen, and wherein said hydrocarbyllink may optionally be substituted with one or more substituentsindependently selected from H, F, Cl, Br, I, CN, OH, SH, NO₂,NR^(x)R^(y), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, S(═O)_(n)(C₁-C₆ alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl,and oxo.

In another embodiment, Ar¹ is substituted phenyl having one or moresubstituents independently selected from OCF₃, OCF₂CF₃, and CF₃.

In another embodiment, Het is substituted pyrazolyl wherein saidsubstituted pyrazolyl has one or more substituents independentlyselected from H, C(═O)O(C₁-C₆ alkyl), or C(═O)NR^(x)R^(y).

In another embodiment, Het is 1,2,4-triazolyl.

In another embodiment, Ar² is phenyl.

In another embodiment, Ar² is substituted phenyl having one or moresubstituents independently selected from H, F, Cl, Br, I, CN, C₁-C₆alkyl, and C₁-C₆ alkoxy.

In another embodiment, R¹ is H or C₁-C₆ alkyl.

In another embodiment, R² is H or C₁-C₆ alkyl.

In another embodiment, each R⁴, R⁵, R⁶, or R⁷ is independently H, F, Cl,or C₁-C₆ alkyl.

In another embodiment, each R⁴, R⁵, R⁶, or R⁷ is independently H or aC₁-C₆ alkyl.

In another embodiment, each R⁴, R⁵, R⁶, or R⁷ is independently H, F orC₁.

In another embodiment, each of R¹ and R² is independently H or a C₁-C₆alkyl.

In another embodiment, R¹ and R² together form a 5-membered saturated orunsaturated ring containing one or two C═O, and such ring is optionallysubstituted with H, OH, F, Cl, Br, I, CN, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, phenyl or phenoxy.

In another embodiment, R³ is substituted phenyl with one or more OH, F,Cl, Br, I, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkenyl, C₁-C₆haloalkenyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, NR^(x)R^(y), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ haloalkyl), C₁-C₆ alkoxy, orC₁-C₆ haloalkoxy.

In another embodiment, the molecule has a structure selected fromcompounds listed in Table 1 below:

TABLE 1 Structures for Compounds A1

A2

A3

A4

A5

A6

A7

A8

A9

A10

A11

A12

A13

A14

A15

A16

A17

A18

A19

A20

A21

A22

A23

A24

A25

A26

A27

A28

A29

A30

A31

A32

A33

A34

A35

A36

A37

A38

A39

A40

A41

A42

A43

A44

A45

A46

A47

A48

A49

A50

A51

A52

A53

A54

A55

Preparation of Triaryl Alcohols

Alcohol analogs can be prepared as shown in Scheme 1 below. A triarylaldehyde 1-1, wherein Het, Ar¹, and Ar² are as disclosed above, may betreated under Wittig olefination conditions such asmethyltriphenylphosphonium bromide in the presence of a base such as1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and in a polar, aprotic solventsuch as tetrahydrofuran (THF) at the reflux temperature to provide thealkene 1-2, wherein Het, Ar¹, and Ar² are as disclosed above (Scheme 1,step a). The alkene 1-2, wherein Het, Ar¹, and Ar² are as disclosedabove, can be reacted under hydroboration-oxidation conditions to affordthe corresponding alcohol 1-3a, wherein Het, Ar¹, and Ar² are asdisclosed above, by reaction with 9-borabicyclo[3.3.1]nonane (9-BBN) and30% hydrogen peroxide in a polar, aprotic solvent such as THF andaqueous sodium hydroxide at ambient temperature (Scheme 1, step b). Thetriaryl alkene 1-2, wherein Het, Ar¹, and Ar² are as disclosed above,can be treated with meta-chloroperoxybenzoic acid (m-CPBA) in an aproticsolvent, such as dichloromethane at ambient temperature to provide thetriaryl epoxide 1-4, wherein Het, Ar¹, and Ar² are as disclosed above(Scheme 1, step c). Opening of the epoxide and further functionalizationcan be achieved by reaction of the triaryl epoxide 1-4, wherein Het,Ar¹, and Ar² are as disclosed above, with either pyridine hydrofluorideat a temperature from 0° C. to ambient temperature to afford 1-3b, ortrichloroisocyanuric acid in the presence of triphenylphosphine and in apolar, aprotic solvent such as acetonitrile at ambient temperature toprovide 1-3c, wherein Het, Ar¹, and Ar² are as disclosed above (Scheme1, steps d and e).

Alcohol analogs can be prepared as shown in Scheme 2 below. A triarylbromide 2-1, wherein Het, Ar¹, and Ar² are as disclosed above, may betreated with pentane-2,4-dione in the presence of a catalyst such ascopper(I) iodide and a base such as potassium phosphate in a polar,aprotic solvent such as dimethyl sulfoxide (DMSO) at the temperature ofabout 90° C. to provide the ketone 2-2, wherein Het, Ar¹, and Ar² are asdisclosed above (Scheme 2, step a). The ketone 2-2, wherein Het, Ar¹,and Ar² are as disclosed above, can be reduced to the correspondingalcohol 2-3, wherein Het, Ar¹, and Ar² are as disclosed above, byreaction with sodium borohydride in a polar, protic solvent such asethanol at ambient temperature (Scheme 2, step b). The triaryl bromide2-1, wherein Het, Ar¹, and Ar² are as disclosed above, may betransformed into the corresponding triaryl iodide 2-4, wherein Het, Ar¹,and Ar² are as disclosed above, using sodium iodide in the presence of acatalyst such as copper(I) iodide and a base such as(1R,2R)—N₁,N₂-dimethylcyclohexane-1,2-diamine in a polar, aproticsolvent such as dioxane at the temperature of about 100° C. (Scheme 2,step c). The triaryl amide 2-5 can be prepared in two steps. Reaction ofa triaryl iodide 2-4, wherein Het, Ar¹, and Ar² are as disclosed above,with copper and ethyl 2-bromo-2,2-difluoroacetate in the presence of apolar, aprotic solvent such as DMSO at a temperature of about 60° C. togive the difluoroacetate ethyl ester (not shown, Scheme 2, step d).Reaction of the ester with a solution of ammonia in methanol in a polar,protic solvent such as methanol at ambient temperature affords the amide2-5, wherein Het, Ar¹, and Ar² are as disclosed above (Scheme 3, stepe). Reduction of the triaryl amide 2-5, wherein Het, Ar¹, and Ar² are asdisclosed above, can be accomplished by reaction with a reducing agentsuch as borane-THF complex in a polar, aprotic solvent such as THF at atemperature of about 60° C. to afford the alcohol 2-6, wherein Het, Ar¹,and Ar² are as disclosed above (Scheme 2, step f).

Preparation of Carbamate Analogs

The activated triaryl alcohol 3-2, wherein Het, Ar¹, Ar², and L are aspreviously disclosed, can be generated by treatment of the triarylalcohol 3-1 (Scheme 3) with an activating agent such asbis(2,5-dioxopyrrolidin-1-yl) carbonate in a polar, aprotic solvent,such as acetonitrile, and in the presence of a base, such as pyridine,(Scheme 3, step a). The activated intermediate is then allowed to reactwith a thiourea 3-3, wherein R³, R¹, and R² are as previously disclosed,in a mixed solvent system, such as dichloromethane-water, and in thepresence of a base, such as sodium bicarbonate (Scheme 3, step b) toafford the carbamate 3-4.

Acid and Salt Derivatives and Solvates

The compounds disclosed in this invention can be in the form ofpesticidally acceptable acid addition salts.

By way of non-limiting example, an amine function can form salts withhydrochloric, hydrobromic, sulfuric, phosphoric, acetic, benzoic,citric, malonic, salicylic, malic, fumaric, oxalic, succinic, tartaric,lactic, gluconic, ascorbic, maleic, aspartic, benzenesulfonic,methanesulfonic, ethanesulfonic, hydroxymethanesulfonic, andhydroxyethanesulfonic acids.

Additionally, by way of non-limiting example, an acid function can formsalts including those derived from alkali or alkaline earth metals andthose derived from ammonia and amines. Examples of preferred cationsinclude sodium, potassium, magnesium, and aminium cations.

The salts are prepared by contacting the free base form with asufficient amount of the desired acid to produce a salt. The free baseforms may be regenerated by treating the salt with a suitable diluteaqueous base solution such as dilute aqueous sodium hydroxide (NaOH),potassium carbonate, ammonia, and sodium bicarbonate. As an example, inmany cases, a pesticide is modified to a more water soluble form e.g.2,4-dichlorophenoxy acetic acid dimethyl amine salt is a more watersoluble form of 2,4-dichlorophenoxy acetic acid, a well-known herbicide.

The compounds disclosed in this invention can also form stable complexeswith solvent molecules that remain intact after the non-complexedsolvent molecules are removed from the compounds. These complexes areoften referred to as “solvates.”

Stereoisomers

Certain compounds disclosed in this document can exist as one or morestereoisomers. The various stereoisomers include geometric isomers,diastereomers, and enantiomers. Thus, the compounds disclosed in thisinvention include racemic mixtures, individual stereoisomers, andoptically active mixtures. It will be appreciated by those skilled inthe art that one stereoisomer may be more active than the others.Individual stereoisomers and optically active mixtures may be obtainedby selective synthetic procedures, by conventional synthetic proceduresusing resolved starting materials, or by conventional resolutionprocedures.

Pests

In another embodiment, the invention disclosed in this document can beused to control pests.

In another embodiment, the invention disclosed in this document can beused to control pests of the Phylum Nematoda.

In another embodiment, the invention disclosed in this document can beused to control pests of the Phylum Arthropoda.

In another embodiment, the invention disclosed in this document can beused to control pests of the Subphylum Chelicerata.

In another embodiment, the invention disclosed in this document can beused to control pests of the Class Arachnida.

In another embodiment, the invention disclosed in this document can beused to control pests of the Subphylum Myriapoda.

In another embodiment, the invention disclosed in this document can beused to control pests of the Class Symphyla.

In another embodiment, the invention disclosed in this document can beused to control pests of the Subphylum Hexapoda.

In another embodiment, the invention disclosed in this document can beused to control pests of the Class Insecta.

In another embodiment, the invention disclosed in this document can beused to control Coleoptera (beetles). A non-exhaustive list of thesepests includes, but is not limited to, Acanthoscelides spp. (weevils),Acanthoscelides obtectus (common bean weevil), Agrilus planipennis(emerald ash borer), Agriotes spp. (wireworms), Anoplophora glabripennis(Asian longhorned beetle), Anthonomus spp. (weevils), Anthonomus grandis(boll weevil), Aphidius spp., Apion spp. (weevils), Apogonia spp.(grubs), Ataenius spretulus (Black Turfgrass Ataenius), Atomarialinearis (pygmy mangold beetle), Aulacophora spp., Bothynoderespunctiventris (beet root weevil), Bruchus spp. (weevils), Bruchuspisorum (pea weevil), Cacoesia spp., Callosobruchus maculatus (southerncow pea weevil), Carpophilus hemipteras (dried fruit beetle), Cassidavittata, Cerosterna spp., Cerotoma spp. (chrysomeids), Cerotomatrifurcata (bean leaf beetle), Ceutorhynchus spp. (weevils),Ceutorhynchus assimilis (cabbage seedpod weevil), Ceutorhynchus napi(cabbage curculio), Chaetocnema spp. (chrysomelids), Colaspis spp. (soilbeetles), Conoderus scalaris, Conoderus stigmosus, Conotrachelusnenuphar (plum curculio), Cotinus nitidis (Green June beetle), Criocerisasparagi (asparagus beetle), Cryptolestes ferrugineus (rusty grainbeetle), Cryptolestes pusillus (flat grain beetle), Cryptolestesturcicus (Turkish grain beetle), Ctenicera spp. (wireworms), Curculiospp. (weevils), Cyclocephala spp. (grubs), Cylindrocpturus adspersus(sunflower stem weevil), Deporaus marginatus (mango leaf-cuttingweevil), Dermestes lardarius (larder beetle), Dermestes maculates (hidebeetle), Diabrotica spp. (chrysolemids), Epilachna varivestis (Mexicanbean beetle), Faustinus cubae, Hylobius pales (pales weevil), Hyperaspp. (weevils), Hypera postica (alfalfa weevil), Hyperdoes spp.(Hyperodes weevil), Hypothenemus hampei (coffee berry beetle), Ips spp.(engravers), Lasioderma serricorne (cigarette beetle), Leptinotarsadecemlineata (Colorado potato beetle), Liogenys fuscus, Liogenyssuturalis, Lissorhoptrus oryzophilus (rice water weevil), Lyctus spp.(wood beetles/powder post beetles), Maecolaspis joliveti, Megascelisspp., Melanotus communis, Meligethes spp., Meligethes aeneus (blossombeetle), Melolontha melolontha (common European cockchafer), Obereabrevis, Oberea linearis, Oryctes rhinoceros (date palm beetle),Oryzaephilus mercator (merchant grain beetle), Oryzaephilus surinamensis(sawtoothed grain beetle), Otiorhynchus spp. (weevils), Oulema melanopus(cereal leaf beetle), Oulema oryzae, Pantomorus spp. (weevils),Phyllophaga spp. (May/June beetle), Phyllophaga cuyabana, Phyllotretaspp. (chrysomelids), Phynchites spp., Popillia japonica (Japanesebeetle), Prostephanus truncates (larger grain borer), Rhizoperthadominica (lesser grain borer), Rhizotrogus spp. (European chafer),Rhynchophorus spp. (weevils), Scolytus spp. (wood beetles), Shenophorusspp. (Billbug), Sitona lineatus (pea leaf weevil), Sitophilus spp.(grain weevils), Sitophilus granaries (granary weevil), Sitophilusoryzae (rice weevil), Stegobium paniceum (drugstore beetle), Triboliumspp. (flour beetles), Tribolium castaneum (red flour beetle), Triboliumconfusum (confused flour beetle), Trogoderma variabile (warehousebeetle), and Zabrus tenebioides.

In another embodiment, the invention disclosed in this document can beused to control Dermaptera (earwigs).

In another embodiment, the invention disclosed in this document can beused to control Dictyoptera (cockroaches). A non-exhaustive list ofthese pests includes, but is not limited to, Blattella germanica (Germancockroach), Blatta orientalis (oriental cockroach), Parcoblattapennylvanica, Periplaneta americana (American cockroach), Periplanetaaustraloasiae (Australian cockroach), Periplaneta brunnea (browncockroach), Periplaneta fuliginosa (smokybrown cockroach), Pyncoselussuninamensis (Surinam cockroach), and Supella longipalpa (brownbandedcockroach).

In another embodiment, the invention disclosed in this document can beused to control Diptera (true flies). A non-exhaustive list of thesepests includes, but is not limited to, Aedes spp. (mosquitoes), Agromyzafrontella (alfalfa blotch leafminer), Agromyza spp. (leaf miner flies),Anastrepha spp. (fruit flies), Anastrepha suspensa (Caribbean fruitfly), Anopheles spp. (mosquitoes), Batrocera spp. (fruit flies),Bactrocera cucurbitae (melon fly), Bactrocera dorsalis (oriental fruitfly), Ceratitis spp. (fruit flies), Ceratitis capitata (Mediterraneanfruit fly), Chrysops spp. (deer flies), Cochlomyia spp. (screwworms),Contarinia spp. (gall midges), Culex spp. (mosquitoes), Dasineura spp.(gall midges), Dasineura brassicae (cabbage gall midge), Delia spp.,Delia platura (seedcorn maggot), Drosophila spp. (vinegar flies), Fanniaspp. (filth flies), Fannia canicularis (little house fly), Fanniascalaris (latrine fly), Gasterophilus intestinalis (horse bot fly),Gracillia perseae, Haematobia irritans (horn fly), Hylemyia spp. (rootmaggots), Hypoderma lineatum (common cattle grub), Liriomyza spp.(leafminer flies), Liriomyza brassica (serpentine leafminer), Melophagusovinus (sheep ked), Musca spp. (muscid flies), Musca autumnalis (facefly), Musca domestica (housefly), Oestrus ovis (sheep bot fly),Oscinella frit (frit fly), Pegomyia betae (beet leafminer), Phorbiaspp., Psila rosae (carrot rust fly), Rhagoletis cerasi (cherry fruitfly), Rhagoletis pomonella (apple maggot), Sitodiplosis mosellana(orange wheat blossom midge), Stomoxys calcitrans (stable fly), Tabanusspp. (horse flies), and Tipula spp. (crane flies).

In another embodiment, the invention disclosed in this document can beused to control Hemiptera (true bugs). A non-exhaustive list of thesepests includes, but is not limited to, Acrosternum hilare (green stinkbug), Blissus leucopterus (chinch bug), Calocoris norvegicus (potatomirid), Cimex hemipterus (tropical bed bug), Cimex lectularius (bedbug), Dagbertus fasciatus, Dichelops furcatus, Dysdercus suturellus(cotton stainer), Edessa meditabunda, Eurygaster maura (cereal bug),Euschistus heros, Euschistus servus (brown stink bug), Helopeltisantonii, Helopeltis theivora (tea blight plantbug), Lagynotomus spp.(stink bugs), Leptocorisa oratorius, Leptocorisa varicornis, Lygus spp.(plant bugs), Lygus hesperus (western tarnished plant bug),Maconellicoccus hirsutus, Neurocolpus longirostris, Nezara viridula(southern green stink bug), Phytocoris spp. (plant bugs), Phytocoriscalifornicus, Phytocoris relativus, Piezodorus guildingi, Poecilocapsuslineatus (fourlined plant bug), Psallus vaccinicola, Pseudacystaperseae, Scaptocoris castanea, and Triatoma spp. (bloodsucking conenosebugs/kissing bugs).

In another embodiment, the invention disclosed in this document can beused to control Homoptera (aphids, scales, whiteflies, leafhoppers). Anon-exhaustive list of these pests includes, but is not limited to,Acrythosiphon pisum (pea aphid), Adelges spp. (adelgids), Aleurodesproletella (cabbage whitefly), Aleurodicus disperses, Aleurothrixusfloccosus (woolly whitefly), Aluacaspis spp., Amrasca bigutellabigutella, Aphrophora spp. (leafhoppers), Aonidiella aurantii(California red scale), Aphis spp. (aphids), Aphis gossypii (cottonaphid), Aphis pomi (apple aphid), Aulacorthum solani (foxglove aphid),Bemisia spp. (whiteflies), Bemisia argentifolii, Bemisia tabaci(sweetpotato whitefly), Brachycolus noxius (Russian aphid),Brachycorynella asparagi (asparagus aphid), Brevennia rehi, Brevicorynebrassicae (cabbage aphid), Ceroplastes spp. (scales), Ceroplastes rubens(red wax scale), Chionaspis spp. (scales), Chrysomphalus spp. (scales),Coccus spp. (scales), Dysaphis plantaginea (rosy apple aphid), Empoascaspp. (leafhoppers), Eriosoma lanigerum (woolly apple aphid), Iceryapurchasi (cottony cushion scale), Idioscopus nitidulus (mangoleafhopper), Laodelphax striatellus (smaller brown planthopper),Lepidosaphes spp., Macrosiphum spp., Macrosiphum euphorbiae (potatoaphid), Macrosiphum granarium (English grain aphid), Macrosiphum rosae(rose aphid), Macrosteles quadrilineatus (aster leafhopper), Mahanarvafrimbiolata, Metopolophium dirhodum (rose grain aphid), Mictislongicornis, Myzus persicae (green peach aphid), Nephotettix spp.(leafhoppers), Nephotettix cinctipes (green leafhopper), Nilaparvatalugens (brown planthopper), Parlatoria pergandii (chaff scale),Parlatoria ziziphi (ebony scale), Peregrinus maidis (corn delphacid),Philaenus spp. (spittlebugs), Phylloxera vitifoliae (grape phylloxera),Physokermes piceae (spruce bud scale), Planococcus spp. (mealybugs),Pseudococcus spp. (mealybugs), Pseudococcus brevipes (pineapplemealybug), Quadraspidiotus perniciosus (San Jose scale), Rhapalosiphumspp. (aphids), Rhapalosiphum maida (corn leaf aphid), Rhapalosiphum padi(oat bird-cherry aphid), Saissetia spp. (scales), Saissetia oleae (blackscale), Schizaphis graminum (greenbug), Sitobion avenae (English grainaphid), Sogatella furcifera (white-backed planthopper), Therioaphis spp.(aphids), Toumeyella spp. (scales), Toxoptera spp. (aphids),Trialeurodes spp. (whiteflies), Trialeurodes vaporariorum (greenhousewhitefly), Trialeurodes abutiloneus (bandedwing whitefly), Unaspis spp.(scales), Unaspis yanonensis (arrowhead scale), and Zulia entreriana.

In another embodiment, the invention disclosed in this document can beused to control Hymenoptera (ants, wasps, and bees). A non-exhaustivelist of these pests includes, but is not limited to, Acromyrrmex spp.,Athalia rosae, Atta spp. (leafcutting ants), Camponotus spp. (carpenterants), Diprion spp. (sawflies), Formica spp. (ants), Iridomyrmex humilis(Argentine ant), Monomorium ssp., Monomorium minumum (little black ant),Monomorium pharaonis (Pharaoh ant), Neodiprion spp. (sawflies),Pogonomyrmex spp. (harvester ants), Polistes spp. (paper wasps),Solenopsis spp. (fire ants), Tapoinoma sessile (odorous house ant),Tetranomorium spp. (pavement ants), Vespula spp. (yellow jackets), andXylocopa spp. (carpenter bees).

In another embodiment, the invention disclosed in this document can beused to control Isoptera (termites). A non-exhaustive list of thesepests includes, but is not limited to, Coptotermes spp., Coptotermescurvignathus, Coptotermes frenchii, Coptotermes formosanus (Formosansubterranean termite), Cornitermes spp. (nasute termites), Cryptotermesspp. (drywood termites), Heterotermes spp. (desert subterraneantermites), Heterotermes aureus, Kalotermes spp. (drywood termites),Incistitermes spp. (drywood termites), Macrotermes spp. (fungus growingtermites), Marginitermes spp. (drywood termites), Microcerotermes spp.(harvester termites), Microtermes obesi, Procornitermes spp.,Reticulitermes spp. (subterranean termites), Reticulitermes banyulensis,Reticulitermes grassei, Reticulitermes flavipes (eastern subterraneantermite), Reticulitermes hageni, Reticulitermes hesperus (westernsubterranean termite), Reticulitermes santonensis, Reticulitermessperatus, Reticulitermes tibialis, Reticulitermes virginicus,Schedorhinotermes spp., and Zootermopsis spp. (rotten-wood termites).

In another embodiment, the invention disclosed in this document can beused to control Lepidoptera (moths and butterflies). A non-exhaustivelist of these pests includes, but is not limited to, Achoea janata,Adoxophyes spp., Adoxophyes orana, Agrotis spp. (cutworms), Agrotisipsilon (black cutworm), Alabama argillacea (cotton leafworm), Amorbiacuneana, Amyelosis transitella (navel orangeworm), Anacamptodesdefectaria, Anarsia lineatella (peach twig borer), Anomis sabubfera(jute looper), Anticarsia gemmatalis (velvetbean caterpillar), Archipsargyrospila (fruit tree leafroller), Archips rosana (rose leaf roller),Argyrotaenia spp. (tortricid moths), Argyrotaenia citrana (orangetortrix), Autographa gamma, Bonagota cranaodes, Borbo cinnara (rice leaffolder), Bucculatrix thurberiella (cotton leaf perforator), Caloptiliaspp. (leaf miners), Capua reticulana, Carposina niponensis (peach fruitmoth), Chilo spp., Chlumetia transversa (mango shoot borer),Choristoneura rosaceana (oblique banded leaf roller), Chrysodeixis spp.,Cnaphalocerus medinalis (grass leafroller), Colas spp., Conpomorphacramerella, Cossus cossus (carpenter moth), Crambus spp. (Sod webworms),Cydia funebrana (plum fruit moth), Cydia molesta (oriental fruit moth),Cydia nignicana (pea moth), Cydia pomonella (codling moth), Darnadiducta, Diaphania spp. (stem borers), Diatraea spp. (stalk borers),Diatraea saccharalis (sugarcane borer), Diatraea graniosella(southwestern corn borer), Earias spp. (bollworms), Earias insulata(Egyptian bollworm), Earias vitella (rough northern bollworm),Ecdytopopha aurantianum, Elasmopalpus lignosellus (lesser cornstalkborer), Epiphysias postruttana (light brown apple moth), Ephestia spp.(flour moths), Ephestia cautella (almond moth), Ephestia elutella(tobacco moth), Ephestia kuehniella (Mediterranean flour moth), Epimecesspp., Epinotia aporema, Erionota thrax (banana skipper), Eupoeciliaambiguella (grape berry moth), Euxoa auxiliaris (army cutworm), Feltiaspp. (cutworms), Gortyna spp. (stemborers), Grapholita molesta (orientalfruit moth), Hedylepta indicata (bean leaf webber), Helicoverpa spp.(noctuid moths), Helicoverpa armigera (cotton bollworm), Helicoverpa zea(bollworm/corn earworm), Heliothis spp. (noctuid moths), Heliothisvirescens (tobacco budworm), Hellula undalis (cabbage webworm),Indarbela spp. (root borers), Keiferia lycopersicella (tomato pinworm),Leucinodes orbonalis (eggplant fruit borer), Leucoptera malifoliella,Lithocollectis spp., Lobesia botrana (grape fruit moth), Loxagrotis spp.(noctuid moths), Loxagrotis albicosta (western bean cutworm), Lymantriadispar (gypsy moth), Lyonetia clerkella (apple leaf miner), Mahasenacorbetti (oil palm bagworm), Malacosoma spp. (tent caterpillars),Mamestra brassicae (cabbage armyworm), Maruca testulalis (bean podborer), Metisa plana (bagworm), Mythimna unipuncta (true armyworm),Neoleucinodes elegantalis (small tomato borer), Nymphula depunctalis(rice caseworm), Operophthera brumata (winter moth), Ostrinia nubilalis(European corn borer), Oxydia vesulia, Pandemis cerasana (common curranttortrix), Pandemis heparana (brown apple tortrix), Papilio demodocus,Pectinophora gossypiella (pink bollworm), Peridroma spp. (cutworms),Peridroma saucia (variegated cutworm), Perileucoptera coffeella (whitecoffee leafminer), Phthorimaea operculella (potato tuber moth),Phyllocnisitis citrella, Phyllonorycter spp. (leafminers), Pieris rapae(imported cabbageworm), Plathypena scabra, Plodia interpunctella (Indianmeal moth), Plutella xylostella (diamondback moth), Polychrosis viteana(grape berry moth), Prays endocarpa, Prays oleae (olive moth),Pseudaletia spp. (noctuid moths), Pseudaletia unipunctata (armyworm),Pseudoplusia includens (soybean looper), Rachiplusia nu, Scirpophagaincertulas, Sesamia spp. (stemborers), Sesamia inferens (pink rice stemborer), Sesamia nonagrioides, Setora nitens, Sitotroga cerealella(Angoumois grain moth), Sparganothis pilleriana, Spodoptera spp.(armyworms), Spodoptera exigua (beet armyworm), Spodoptera frugiperda(fall armyworm), Spodoptera oridania (southern armyworm), Synanthedonspp. (root borers), Thecla basilides, Thermisia gemmatalis, Tineolabisselliella (webbing clothes moth), Trichoplusia ni (cabbage looper),Tuta absoluta, Yponomeuta spp., Zeuzera coffeae (red branch borer), andZeuzera pyrina (leopard moth).

In another embodiment, the invention disclosed in this document can beused to control Mallophaga (chewing lice). A non-exhaustive list ofthese pests includes, but is not limited to, Bovicola ovis (sheep bitinglouse), Menacanthus stramineus (chicken body louse), and Menopongallinea (common hen louse).

In another embodiment, the invention disclosed in this document can beused to control Orthoptera (grasshoppers, locusts, and crickets). Anon-exhaustive list of these pests includes, but is not limited to,Anabrus simplex (Mormon cricket), Gryllotalpidae (mole crickets),Locusta migratoria, Melanoplus spp. (grasshoppers), Microcentrumretinerve (angular winged katydid), Pterophylla spp. (katydids),chistocerca gregaria, Scudderia furcata (fork tailed bush katydid), andValanga nigricorni.

In another embodiment, the invention disclosed in this document can beused to control Phthiraptera (sucking lice). A non-exhaustive list ofthese pests includes, but is not limited to, Haematopinus spp. (cattleand hog lice), Linognathus ovillus (sheep louse), Pediculus humanuscapitis (human body louse), Pediculus humanus humanus (human body lice),and Pthirus pubis (crab louse),

In another embodiment, the invention disclosed in this document can beused to control Siphonaptera (fleas). A non-exhaustive list of thesepests includes, but is not limited to, Ctenocephalides canis (dog flea),Ctenocephalides felis (cat flea), and Pulex irritans (human flea).

In another embodiment, the invention disclosed in this document can beused to control Thysanoptera (thrips). A non-exhaustive list of thesepests includes, but is not limited to, Frankliniella fusca (tobaccothrips), Frankliniella occidentalis (western flower thrips),Frankliniella shultzei Frankliniella williamsi (corn thrips),Heliothrips haemorrhaidalis (greenhouse thrips), Riphiphorothripscruentatus, Scirtothrips spp., Scirtothrips citri (citrus thrips),Scirtothrips dorsalis (yellow tea thrips), Taeniothripsrhopalantennalis, and Thrips spp.

In another embodiment, the invention disclosed in this document can beused to control Thysanura (bristletails). A non-exhaustive list of thesepests includes, but is not limited to, Lepisma spp. (silverfish) andThermobia spp. (firebrats).

In another embodiment, the invention disclosed in this document can beused to control Acarina (mites and ticks). A non-exhaustive list ofthese pests includes, but is not limited to, Acarapsis woodi (trachealmite of honeybees), Acarus spp. (food mites), Acarus siro (grain mite),Aceria mangiferae (mango bud mite), Aculops spp., Aculops lycopersici(tomato russet mite), Aculops pelekasi, Aculus pelekassi, Aculusschlechtendali (apple rust mite), Amblyomma americanum (lone star tick),Boophilus spp. (ticks), Brevipalpus obovatus (privet mite), Brevipalpusphoenicis (red and black flat mite), Demodex spp. (mange mites),Dermacentor spp. (hard ticks), Dermacentor variabilis (American dogtick), Dermatophagoides pteronyssinus (house dust mite), Eotetranycusspp., Eotetranychus carpini (yellow spider mite), Epitimerus spp.,Eriophyes spp., Ixodes spp. (ticks), Metatetranycus spp., Notoedrescati, Oligonychus spp., Oligonychus coffee, Oligonychus ilicus (southernred mite), Panonychus spp., Panonychus citri (citrus red mite),Panonychus ulmi (European red mite), Phyllocoptruta oleivora (citrusrust mite), Polyphagotarsonemun latus (broad mite), Rhipicephalussanguineus (brown dog tick), Rhizoglyphus spp. (bulb mites), Sarcoptesscabiei (itch mite), Tegolophus perseaflorae, Tetranychus spp.,Tetranychus urticae (two-spotted spider mite), and Varroa destructor(honey bee mite).

In another embodiment, the invention disclosed in this document can beused to control Nematoda (nematodes). A non-exhaustive list of thesepests includes, but is not limited to, Aphelenchoides spp. (bud and leaf& pine wood nematodes), Belonolaimus spp. (sting nematodes),Criconemella spp. (ring nematodes), Dirofilaria immitis (dog heartworm),Ditylenchus spp. (stem and bulb nematodes), Heterodera spp. (cystnematodes), Heterodera zeae (corn cyst nematode), Hirschmanniella spp.(root nematodes), Hoplolaimus spp. (lance nematodes), Meloidogyne spp.(root knot nematodes), Meloidogyne incognita (root knot nematode),Onchocerca volvulus (hook-tail worm), Pratylenchus spp. (lesionnematodes), Radopholus spp. (burrowing nematodes), and Rotylenchusrenformis (kidney-shaped nematode).

In another embodiment, the invention disclosed in this document can beused to control Symphyla (symphylans). A non-exhaustive list of thesepests includes, but is not limited to, Scutigerella immaculata.

Neonicotinoid-resistant insects are known in the art (see for example WO2012/141754 A2). Compounds of the subject invention disclosed hereinhave the advantage of being superior or at least equal in insecticidalactivity against such neonicotinoid-resistant insects as compared topreviously disclosed compounds. In some embodiments, theneonicotinoid-resistant insect has resistance to at least one of theinsecticides selected from the group consisting of acetamiprid,clothianidin, dinotefuran, flupyradifurone (BYI 02960), imidacloprid,imidaclothiz, nitenpyram, thiacloprid, thiamethoxam, and combinationsthereof. In other embodiments, the combination between the compounds ofthe subject invention and a second pesticide can be used for controllingsuch neonicotinoid-resistant insects. In further embodiments, the secondpesticide is selected from the group consisting of acetamiprid,clothianidin, dinotefuran, flupyradifurone (BYI 02960), imidacloprid,imidaclothiz, nitenpyram, thiacloprid, and thiamethoxam.

Mixtures

The invention disclosed in this document can also be used with variousinsecticides, both for reasons of economy and synergy. Such insecticidesinclude, but are not limited to, antibiotic insecticides, macrocycliclactone insecticides (for example, avermectin insecticides, milbemycininsecticides, and spinosyn insecticides), arsenical insecticides,botanical insecticides, carbamate insecticides (for example,benzofuranyl methylcarbamate insecticides, dimethylcarbamateinsecticides, oxime carbamate insecticides, and phenyl methylcarbamateinsecticides), diamide insecticides, desiccant insecticides,dinitrophenol insecticides, fluorine insecticides, formamidineinsecticides, fumigant insecticides, inorganic insecticides, insectgrowth regulators (for example, chitin synthesis inhibitors, juvenilehormone mimics, juvenile hormones, moulting hormone agonists, moultinghormones, moulting inhibitors, precocenes, and other unclassified insectgrowth regulators), nereistoxin analogue insecticides, nicotinoidinsecticides (for example, nitroguanidine insecticides, nitromethyleneinsecticides, and pyridylmethylamine insecticides), organochlorineinsecticides, organophosphorus insecticides, oxadiazine insecticides,oxadiazolone insecticides, phthalimide insecticides, pyrazoleinsecticides, pyrethroid insecticides, pyrimidinamine insecticides,pyrrole insecticides, tetramic acid insecticides, tetronic acidinsecticides, thiazole insecticides, thiazolidine insecticides, thioureainsecticides, urea insecticides, as well as, other unclassifiedinsecticides.

Some of the particular insecticides that can be employed beneficially incombination with the invention disclosed in this document include, butare not limited to, the following 1,2-dichloropropane,1,3-dichloropropene, abamectin, acephate, acetamiprid, acethion,acetoprole, acrinathrin, acrylonitrile, acynonapyr, afidopyropen,afoxolaner, alanycarb, aldicarb, aldoxycarb, aldrin, allethrin,allosamidin, allyxycarb, alpha-cypermethrin, alpha-endosulfan,amidithion, aminocarb, amiton, amitraz, anabasine, athidathion,azadirachtin, azamethiphos, azinphos-ethyl, azinphos-methyl, azothoate,barium hexafluorosilicate, barthrin, bendiocarb, benfuracarb, bensultap,benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenthrin,bioallethrin, bioethanomethrin, biopermethrin, bioresmethrin,bistrifluron, borax, boric acid, broflanilide, bromfenvinfos,bromocyclen, bromo-DDT, bromophos, bromophos-ethyl, bufencarb,buprofezin, butacarb, butathiofos, butocarboxim, butonate,butoxycarboxim, cadusafos, calcium arsenate, calcium polysulfide,camphechlor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbontetrachloride, carbophenothion, carbosulfan, cartap,chlorantraniliprole, chlorbicyclen, chlordane, chlordecone,chlordimeform, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chloroform, chloropicrin,chloroprallethrin, chlorphoxim, chlorprazophos, chlorpyrifos,chlorpyrifos-methyl, chlorthiophos, chromafenozide, cinerin I, cinerinII, cismethrin, cloethocarb, closantel, clothianidin, copperacetoarsenite, copper arsenate, copper naphthenate, copper oleate,coumaphos, coumithoate, crotamiton, crotoxyphos, crufomate, cryolite,cyanofenphos, cyanophos, cyanthoate, cyantraniliprole, cyclaniliprole,cyclethrin, cycloprothrin, cycloxaprid, cyfluthrin, cyhalothrin,cyhalodiamide, cypermethrin, cyphenothrin, cyromazine, cythioate, DDT,decarbofuran, deltamethrin, demephion, demephion-O, demephion-S,demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S,demeton-S-methyl, demeton-S-methylsulphon, diafenthiuron, dialifos,diatomaceous earth, diazinon, dicapthon, dichlofenthion, dichlorvos,dicloromezotiaz, dicresyl, dicrotophos, dicyclanil, dieldrin,diflubenzuron, dilor, dimefluthrin, dimefox, dimetan, dimethoate,dimethrin, dimethylvinphos, dimetilan, dimpropyridaz, dinex, dinoprop,dinosam, dinotefuran, diofenolan, dioxabenzofos, dioxacarb, dioxathion,disulfoton, dithicrofos, d-limonene, DNOC, doramectin, ecdysterone,emamectin, EMPC, empenthrin, endosulfan, endothion, endrin, EPN,epofenonane, eprinomectin, epsilon-metofluthrin, epsilon-momfluorothrin,esfenvalerate, etaphos, ethiofencarb, ethion, ethiprole, ethoate-methyl,ethoprophos, ethyl formate, ethyl-DDD, ethylene dibromide, ethylenedichloride, ethylene oxide, etofenprox, etrimfos, EXD, famphur,fenamiphos, fenazaflor, fenchlorphos, fenethacarb, fenfluthrin,fenitrothion, fenobucarb, fenoxacrim, fenoxycarb, fenpirithrin,fenpropathrin, fensulfothion, fenthion, fenthion-ethyl, fenvalerate,fipronil, flonicamid, flubendiamide, flucofuron, flucycloxuron,flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole,fluhexafon, flupyradifurone, flupyrimin, fluralaner, fluvalinate,fluxametamide, fonofos, formetanate, formothion, formparanate,fosmethilan, fospirate, fosthietan, furathiocarb, furethrin,gamma-cyhalothrin, gamma-HCH, halfenprox, halofenozide, HCH, HEOD,heptachlor, heptenophos, heterophos, hexaflumuron, HHDN, hydramethylnon,hydrogen cyanide, hydroprene, hyquincarb, imidacloprid, imidaclothiz,imiprothrin, indoxacarb, iodomethane, IPSP, isazofos, isobenzan,isocarbophos, isocycloseram, isodrin, isofenphos, isoprocarb,isoprothiolane, isothioate, isoxathion, ivermectin, jasmolin I, jasmolinII, jodfenphos, juvenile hormone I, juvenile hormone II, juvenilehormone III, kappa-bifenthrin, kappa-tefluthrin, kelevan, kinoprene,lambda-cyhalothrin, lead arsenate, lepimectin, leptophos, lindane,lirimfos, lotilaner, lufenuron, lythidathion, malathion, malonoben,mazidox, mecarbam, mecarphon, menazon, meperfluthrin, mephosfolan,mercurous chloride, mesulfenfos, metaflumizone, methacrifos,methamidophos, methidathion, methiocarb, methocrotophos, methomyl,methoprene, methoxychlor, methoxyfenozide, methyl bromide,methylchloroform, methylene chloride, metofluthrin, metolcarb,metoxadiazone, mevinphos, mexacarbate, milbemectin, milbemycin oxime,mipafox, mirex, momfluorothrin, monocrotophos, morphothion, moxidectin,naftalofos, naled, naphthalene, nicotine, nifluridide, nitenpyram,nithiazine, nitrilacarb, novaluron, noviflumuron, omethoate, oxamyl,oxazosulfyl, oxydemeton-methyl, oxydeprofos, oxydisulfoton,paichongding, para-dichlorobenzene, parathion, parathion-methyl,penfluron, pentachlorophenol, permethrin, phenkapton, phenothrin,phenthoate, phorate, phosalone, phosfolan, phosmet, phosnichlor,phosphamidon, phosphine, phoxim, phoxim-methyl, pirimetaphos,pirimicarb, pirimiphos-ethyl, pirimiphos-methyl, potassium arsenite,potassium thiocyanate, pp′-DDT, prallethrin, precocene I, precocene II,precocene III, primidophos, profenofos, profluthrin, promacyl,promecarb, propaphos, propetamphos, propoxur, prothidathion, prothiofos,prothoate, protrifenbute, pyraclofos, pyrafluprole, pyrazophos,pyresmethrin, pyrethrin I, pyrethrin II, pyridaben, pyridalyl,pyridaphenthion, pyrifluquinazon, pyrimidifen, pyrimitate, pyriprole,pyriproxyfen, quassia, quinalphos, quinalphos-methyl, quinothion,rafoxanide, resmethrin, rotenone, ryania, sabadilla, schradan,selamectin, silafluofen, silica gel, sodium arsenite, sodium fluoride,sodium hexafluorosilicate, sodium thiocyanate, sarolaner, sophamide,spinetoram, spinosad, spiromesifen, spiropidion, spirotetramat,sulcofuron, sulfoxaflor, sulfluramid, sulfotep, sulfuryl fluoride,sulprofos, tau-fluvalinate, tazimcarb, TDE, tebufenozide, tebufenpyrad,tebupirimfos, teflubenzuron, tefluthrin, temephos, TEPP, terallethrin,terbufos, tetrachloroethane, tetrachlorvinphos, tetramethrin,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,theta-cypermethrin, thiacloprid, thiamethoxam, thicrofos, thiocarboxime,thiocyclam, thiodicarb, thiofanox, thiometon, thiosultap, thuringiensin,tolfenpyrad, tralomethrin, transfluthrin, transpermethrin, triarathene,triazamate, triazophos, trichlorfon, trichlormetaphos-3, trichloronat,trifenofos, triflumezopyrim, triflumuron, trimethacarb, triprene,tyclopyrazoflor, vamidothion, vaniliprole, XMC, xylylcarb,zeta-cypermethrin, zolaprofos, and α-ecdysone.

Additionally, any combination of the above insecticides can be used.

The invention disclosed in this document can also be used, for reasonsof economy and synergy, with acaricides, algicides, antifeedants,avicides, bactericides, bird repellents, chemosterilants, fungicides,herbicide safeners, herbicides, insect attractants, insect repellents,mammal repellents, mating disrupters, molluscicides, plant activators,plant growth regulators, rodenticides, synergists, defoliants,desiccants, disinfectants, semiochemicals, and virucides (thesecategories not necessarily mutually exclusive).

Synergistic Mixtures

The invention disclosed in this document can be used with othercompounds such as the ones mentioned under the heading “Mixtures” toform synergistic mixtures where the mode of action of the compounds inthe mixtures are the same, similar, or different.

Examples of mode of actions include, but are not limited to:acetylcholinesterase inhibitor; sodium channel modulator; chitinbiosynthesis inhibitor; GABA-gated chloride channel antagonist; GABA-and glutamate-gated chloride channel agonist; acetylcholine receptoragonist; MET I inhibitor; Mg-stimulated ATPase inhibitor; nicotinicacetylcholine receptor; Midgut membrane disrupter; oxidativephosphorylation disrupter, and ryanodine receptor (RyRs).

Additionally, the following compounds are known as synergists and can beused with the invention disclosed in this document: piperonyl butoxide,piprotal, propyl isome, sesamex, sesamolin, and sulfoxide.

Formulations

A pesticide is rarely suitable for application in its pure form. It isusually necessary to add other substances so that the pesticide can beused at the required concentration and in an appropriate form,permitting ease of application, handling, transportation, storage, andmaximum pesticide activity. Thus, pesticides are formulated into, forexample, baits, concentrated emulsions, dusts, emulsifiableconcentrates, fumigants, gels, granules, microencapsulations, seedtreatments, suspension concentrates, suspoemulsions, tablets, watersoluble liquids, water dispersible granules or dry flowables, wettablepowders, and ultra low volume solutions.

Pesticides are applied most often as aqueous suspensions or emulsionsprepared from concentrated formulations of such pesticides. Suchwater-soluble, water-suspendable, or emulsifiable formulations, areeither solids, usually known as wettable powders, or water dispersiblegranules, or liquids usually known as emulsifiable concentrates, oraqueous suspensions. Wettable powders, which may be compacted to formwater dispersible granules, comprise an intimate mixture of thepesticide, a carrier, and surfactants. The concentration of thepesticide is usually from about 10% to about 90% by weight. The carrieris usually chosen from among the attapulgite clays, the montmorilloniteclays, the diatomaceous earths, or the purified silicates. Effectivesurfactants, comprising from about 0.5% to about 10% of the wettablepowder, are found among sulfonated lignins, condensednaphthalenesulfonates, naphthalenesulfonates, alkylbenzenesulfonates,alkyl sulfates, and nonionic surfactants such as ethylene oxide adductsof alkyl phenols.

Emulsifiable concentrates of pesticides comprise a convenientconcentration of a pesticide, such as from about 50 to about 500 gramsper liter of liquid dissolved in a carrier that is either a watermiscible solvent or a mixture of water-immiscible organic solvent andemulsifiers. Useful organic solvents include aromatics, especiallyxylenes and petroleum fractions, especially the high-boilingnaphthalenic and olefinic portions of petroleum such as heavy aromaticnaphtha. Other organic solvents may also be used, such as the terpenicsolvents including rosin derivatives, aliphatic ketones such ascyclohexanone, and complex alcohols such as 2-ethoxyethanol. Suitableemulsifiers for emulsifiable concentrates are chosen from conventionalanionic and nonionic surfactants.

Aqueous suspensions comprise suspensions of water-insoluble pesticidesdispersed in an aqueous carrier at a concentration in the range fromabout 5% to about 50% by weight. Suspensions are prepared by finelygrinding the pesticide and vigorously mixing it into a carrier comprisedof water and surfactants. Ingredients, such as inorganic salts andsynthetic or natural gums, may also be added, to increase the densityand viscosity of the aqueous carrier. It is often most effective togrind and mix the pesticide at the same time by preparing the aqueousmixture and homogenizing it in an implement such as a sand mill, ballmill, or piston-type homogenizer.

Pesticides may also be applied as granular compositions that areparticularly useful for applications to the soil. Granular compositionsusually contain from about 0.5% to about 10% by weight of the pesticide,dispersed in a carrier that comprises clay or a similar substance. Suchcompositions are usually prepared by dissolving the pesticide in asuitable solvent and applying it to a granular carrier which has beenpre-formed to the appropriate particle size, in the range of from about0.5 to about 3 mm. Such compositions may also be formulated by making adough or paste of the carrier and compound and crushing and drying toobtain the desired granular particle size.

Dusts containing a pesticide are prepared by intimately mixing thepesticide in powdered form with a suitable dusty agricultural carrier,such as kaolin clay, ground volcanic rock, and the like. Dusts cansuitably contain from about 1% to about 10% of the pesticide. They canbe applied as a seed dressing or as a foliage application with a dustblower machine.

It is equally practical to apply a pesticide in the form of a solutionin an appropriate organic solvent, usually petroleum oil, such as thespray oils, which are widely used in agricultural chemistry.

Pesticides can also be applied in the form of an aerosol composition. Insuch compositions the pesticide is dissolved or dispersed in a carrier,which is a pressure-generating propellant mixture. The aerosolcomposition is packaged in a container from which the mixture isdispensed through an atomizing valve.

Pesticide baits are formed when the pesticide is mixed with food or anattractant or both. When the pests eat the bait they also consume thepesticide. Baits may take the form of granules, gels, flowable powders,liquids, or solids. They are used in pest harborages.

Fumigants are pesticides that have a relatively high vapor pressure andhence can exist as a gas in sufficient concentrations to kill pests insoil or enclosed spaces. The toxicity of the fumigant is proportional toits concentration and the exposure time. They are characterized by agood capacity for diffusion and act by penetrating the pest'srespiratory system or being absorbed through the pest's cuticle.Fumigants are applied to control stored product pests under gas proofsheets, in gas sealed rooms or buildings or in special chambers.

Pesticides can be microencapsulated by suspending the pesticideparticles or droplets in plastic polymers of various types. By alteringthe chemistry of the polymer or by changing factors in the processing,microcapsules can be formed of various sizes, solubility, wallthicknesses, and degrees of penetrability. These factors govern thespeed with which the active ingredient within is released, which inturn, affects the residual performance, speed of action, and odor of theproduct.

Oil solution concentrates are made by dissolving pesticide in a solventthat will hold the pesticide in solution. Oil solutions of a pesticideusually provide faster knockdown and kill of pests than otherformulations due to the solvents themselves having pesticidal action andthe dissolution of the waxy covering of the integument increasing thespeed of uptake of the pesticide. Other advantages of oil solutionsinclude better storage stability, better penetration of crevices, andbetter adhesion to greasy surfaces.

Another embodiment is an oil-in-water emulsion, wherein the emulsioncomprises oily globules which are each provided with a lamellar liquidcrystal coating and are dispersed in an aqueous phase, wherein each oilyglobule comprises at least one compound which is agriculturally active,and is individually coated with a monolamellar or oligolamellar layercomprising: (1) at least one nonionic lipophilic surface-active agent,(2) at least one nonionic hydrophilic surface-active agent and (3) atleast one ionic surface-active agent, wherein the globules having a meanparticle diameter of less than 800 nanometers. Further information onthe embodiment is disclosed in U.S. patent publication 20070027034published Feb. 1, 2007, having patent application Ser. No. 11/495,228.For ease of use this embodiment will be referred to as “OIWE”.

Other Formulation Components

Generally, the invention disclosed in this document when used in aformulation, such formulation can also contain other components. Thesecomponents include, but are not limited to, (this is a non-exhaustiveand non-mutually exclusive list) wetters, spreaders, stickers,penetrants, buffers, sequestering agents, drift reduction agents,compatibility agents, anti-foam agents, cleaning agents, andemulsifiers. A few components are described forthwith.

A wetting agent is a substance that when added to a liquid increases thespreading or penetration power of the liquid by reducing the interfacialtension between the liquid and the surface on which it is spreading.Wetting agents are used for two main functions in agrochemicalformulations: during processing and manufacture to increase the rate ofwetting of powders in water to make concentrates for soluble liquids orsuspension concentrates; and during mixing of a product with water in aspray tank to reduce the wetting time of wettable powders and to improvethe penetration of water into water-dispersible granules. Examples ofwetting agents used in wettable powder, suspension concentrate, andwater-dispersible granule formulations are: sodium lauryl sulfate;sodium dioctyl sulfosuccinate; alkyl phenol ethoxylates; and aliphaticalcohol ethoxylates.

A dispersing agent is a substance which adsorbs onto the surface ofparticles and helps to preserve the state of dispersion of the particlesand prevents them from reaggregating. Dispersing agents are added toagrochemical formulations to facilitate dispersion and suspension duringmanufacture, and to ensure the particles redisperse into water in aspray tank. They are widely used in wettable powders, suspensionconcentrates and water-dispersible granules. Surfactants that are usedas dispersing agents have the ability to adsorb strongly onto a particlesurface and provide a charged or steric barrier to reaggregation ofparticles. The most commonly used surfactants are anionic, nonionic, ormixtures of the two types. For wettable powder formulations, the mostcommon dispersing agents are sodium lignosulfonates. For suspensionconcentrates, very good adsorption and stabilization are obtained usingpolyelectrolytes, such as sodium naphthalene sulfonate formaldehydecondensates. Tristyrylphenol ethoxylate phosphate esters are also used.Nonionics such as alkylarylethylene oxide condensates and EO-PO blockcopolymers are sometimes combined with anionics as dispersing agents forsuspension concentrates. In recent years, new types of very highmolecular weight polymeric surfactants have been developed as dispersingagents. These have very long hydrophobic ‘backbones’ and a large numberof ethylene oxide chains forming the ‘teeth’ of a ‘comb’ surfactant.These high molecular weight polymers can give very good long-termstability to suspension concentrates because the hydrophobic backboneshave many anchoring points onto the particle surfaces. Examples ofdispersing agents used in agrochemical formulations are: sodiumlignosulfonates; sodium naphthalene sulfonate formaldehyde condensates;tristyrylphenol ethoxylate phosphate esters; aliphatic alcoholethoxylates; alkyl ethoxylates; EO-PO block copolymers; and graftcopolymers.

An emulsifying agent is a substance which stabilizes a suspension ofdroplets of one liquid phase in another liquid phase. Without theemulsifying agent the two liquids would separate into two immiscibleliquid phases. The most commonly used emulsifier blends containalkylphenol or aliphatic alcohol with twelve or more ethylene oxideunits and the oil-soluble calcium salt of dodecylbenzenesulfonic acid. Arange of hydrophile-lipophile balance (“HLB”) values from 8 to 18 willnormally provide good stable emulsions. Emulsion stability can sometimesbe improved by the addition of a small amount of an EO-PO blockcopolymer surfactant.

A solubilizing agent is a surfactant which will form micelles in waterat concentrations above the critical micelle concentration. The micellesare then able to dissolve or solubilize water-insoluble materials insidethe hydrophobic part of the micelle. The type of surfactants usuallyused for solubilization are nonionics: sorbitan monooleates; sorbitanmonooleate ethoxylates; and methyl oleate esters.

Surfactants are sometimes used, either alone or with other additivessuch as mineral or vegetable oils as adjuvants to spray-tank mixes toimprove the biological performance of the pesticide on the target. Thetypes of surfactants used for bioenhancement depend generally on thenature and mode of action of the pesticide. However, they are oftennonionics such as: alkyl ethoxylates; linear aliphatic alcoholethoxylates; aliphatic amine ethoxylates.

A carrier or diluent in an agricultural formulation is a material addedto the pesticide to give a product of the required strength. Carriersare usually materials with high absorptive capacities, while diluentsare usually materials with low absorptive capacities. Carriers anddiluents are used in the formulation of dusts, wettable powders,granules and water-dispersible granules.

Organic solvents are used mainly in the formulation of emulsifiableconcentrates, ULV (ultra low volume) formulations, and to a lesserextent granular formulations. Sometimes mixtures of solvents are used.The first main groups of solvents are aliphatic paraffinic oils such askerosene or refined paraffins. The second main group and the most commoncomprises the aromatic solvents such as xylene and higher molecularweight fractions of C9 and C10 aromatic solvents. Chlorinatedhydrocarbons are useful as cosolvents to prevent crystallization ofpesticides when the formulation is emulsified into water. Alcohols aresometimes used as cosolvents to increase solvent power.

Thickeners or gelling agents are used mainly in the formulation ofsuspension concentrates, emulsions and suspoemulsions to modify therheology or flow properties of the liquid and to prevent separation andsettling of the dispersed particles or droplets. Thickening, gelling,and anti-settling agents generally fall into two categories, namelywater-insoluble particulates and water-soluble polymers. It is possibleto produce suspension concentrate formulations using clays and silicas.Examples of these types of materials, include, but are not limited to,montmorillonite, e.g. bentonite; magnesium aluminum silicate; andattapulgite. Water-soluble polysaccharides have been used asthickening-gelling agents for many years. The types of polysaccharidesmost commonly used are natural extracts of seeds and seaweeds or aresynthetic derivatives of cellulose. Examples of these types of materialsinclude, but are not limited to, guar gum; locust bean gum; carrageenam;alginates; methyl cellulose; sodium carboxymethyl cellulose (SCMC);hydroxyethyl cellulose (HEC). Other types of anti-settling agents arebased on modified starches, polyacrylates, polyvinyl alcohol andpolyethylene oxide. Another good anti-settling agent is xanthan gum.

Microorganisms cause spoilage of formulated products. Thereforepreservation agents are used to eliminate or reduce their effect.Examples of such agents include, but are not limited to: propionic acidand its sodium salt; sorbic acid and its sodium or potassium salts;benzoic acid and its sodium salt; p-hydroxybenzoic acid sodium salt;methyl p-hydroxybenzoate; and 1,2-benzisothiazalin-3-one (BIT).

The presence of surfactants, which lower interfacial tension, oftencauses water-based formulations to foam during mixing operations inproduction and in application through a spray tank. In order to reducethe tendency to foam, anti-foam agents are often added either during theproduction stage or before filling into bottles. Generally, there aretwo types of anti-foam agents, namely silicones and non-silicones.Silicones are usually aqueous emulsions of dimethyl polysiloxane whilethe non-silicone anti-foam agents are water-insoluble oils, such asoctanol and nonanol, or silica. In both cases, the function of theanti-foam agent is to displace the surfactant from the air-waterinterface.

Applications

The actual amount of pesticide to be applied to loci of pests isgenerally not critical and can readily be determined by those skilled inthe art. In general, concentrations from about 0.01 grams of pesticideper hectare to about 5000 grams of pesticide per hectare are expected toprovide good control.

The locus to which a pesticide is applied can be any locus inhabited byany pest, for example, vegetable crops, fruit and nut trees, grapevines,ornamental plants, domesticated animals, the interior or exteriorsurfaces of buildings, and the soil around buildings. Controlling pestsgenerally means that pest populations, activity, or both, are reduced ina locus. This can come about when: pest populations are repulsed from alocus; when pests are incapacitated in or around a locus; or pests areexterminated, in whole or in part, in or around a locus. Of course acombination of these results can occur. Generally, pest populations,activity, or both are desirably reduced more than fifty percent,preferably more than 90 percent.

Generally, with baits, the baits are placed in the ground where, forexample, termites can come into contact with the bait. Baits can also beapplied to a surface of a building, (horizontal, vertical, or slantsurface) where, for example, ants, termites, cockroaches, and flies, cancome into contact with the bait.

Because of the unique ability of the eggs of some pests to resistpesticides repeated applications may be desirable to control newlyemerged larvae.

Systemic movement of pesticides in plants may be utilized to controlpests on one portion of the plant by applying the pesticides to adifferent portion of the plant. For example, control of foliar-feedinginsects can be controlled by drip irrigation or furrow application, orby treating the seed before planting. Seed treatment can be applied toall types of seeds, including those from which plants geneticallytransformed to express specialized traits will germinate. Representativeexamples include those expressing proteins toxic to invertebrate pests,such as Bacillus thuringiensis or other insecticidal toxins, thoseexpressing herbicide resistance, such as “Roundup Ready” seed, or thosewith “stacked” foreign genes expressing insecticidal toxins, herbicideresistance, nutrition-enhancement or any other beneficial traits.Furthermore, such seed treatments with the invention disclosed in thisdocument can further enhance the ability of a plant to better withstandstressful growing conditions. This results in a healthier, more vigorousplant, which can lead to higher yields at harvest time.

It should be readily apparent that the invention can be used with plantsgenetically transformed to express specialized traits, such as Bacillusthuringiensis or other insecticidal toxins, or those expressingherbicide resistance, or those with “stacked” foreign genes expressinginsecticidal toxins, herbicide resistance, nutrition-enhancement or anyother beneficial traits.

The invention disclosed in this document is suitable for controllingendoparasites and ectoparasites in the veterinary medicine sector or inthe field of animal keeping. Compounds are applied in a known manner,such as by oral administration in the form of, for example, tablets,capsules, drinks, granules, by dermal application in the form of, forexample, dipping, spraying, pouring on, spotting on, and dusting, and byparenteral administration in the form of, for example, an injection.

The invention disclosed in this document can also be employedadvantageously in livestock keeping, for example, cattle, sheep, pigs,chickens, and geese. Suitable formulations are administered orally tothe animals with the drinking water or feed. The dosages andformulations that are suitable depend on the species.

Before a pesticide can be used or sold commercially, such pesticideundergoes lengthy evaluation processes by various governmentalauthorities (local, regional, state, national, international).Voluminous data requirements are specified by regulatory authorities andmust be addressed through data generation and submission by the productregistrant or by another on the product registrant's behalf. Thesegovernmental authorities then review such data and if a determination ofsafety is concluded, provide the potential user or seller with productregistration approval. Thereafter, in that locality where the productregistration is granted and supported, such user or seller may use orsell such pesticide.

Combinations

In another embodiment of this invention, molecules of Formula A, FormulaOne, Formula Two or Formula Three may be used in combination (such as,in a compositional mixture, or a simultaneous or sequential application)with one or more active ingredients.

In another embodiment of this invention, molecules of Formula A, FormulaOne, Formula Two or Formula Three may be used in combination (such as,in a compositional mixture, or a simultaneous or sequential application)with one or more active ingredients each having a mode of action (MoA)that is the same as, similar to, but more likely—different from, the MoAof the molecules of Formula A, Formula One, Formula Two or FormulaThree.

In another embodiment, molecules of Formula A, Formula One, Formula Twoor Formula Three may be used in combination (such as, in a compositionalmixture, or a simultaneous or sequential application) with one or moremolecules having acaricidal, algicidal, avicidal, bactericidal,fungicidal, herbicidal, insecticidal, molluscicidal, nematicidal,rodenticidal, and/or virucidal properties.

In another embodiment, the molecules of Formula A, Formula One, FormulaTwo or Formula Three may be used in combination (such as, in acompositional mixture, or a simultaneous or sequential application) withone or more molecules that are antifeedants, bird repellents,chemosterilants, herbicide safeners, insect attractants, insectrepellents, mammal repellents, mating disrupters, plant activators,plant growth regulators, and/or synergists.

In another embodiment, molecules of Formula A, Formula One, Formula Twoor Formula Three may also be used in combination (such as in acompositional mixture, or a simultaneous or sequential application) withone or more biopesticides.

In another embodiment, in a pesticidal composition combinations of amolecule of Formula A, Formula One, Formula Two or Formula Three and anactive ingredient may be used in a wide variety of weight ratios. Forexample, in a two-component mixture, the weight ratio of a molecule ofFormula A, Formula One, Formula Two or Formula Three to an activeingredient, the weight ratios in Table A may be used. However, ingeneral, weight ratios less than about 10:1 to about 1:10 are preferred.It is also preferred sometimes to use a three, four, five, six, seven,or more, component mixture comprising a molecule of Formula A, FormulaOne, Formula Two or Formula Three and an additional two or more activeingredients.

TABLE A Weight Ratios Molecule of the Formula A, Formula One, FormulaTwo or Formula Three: active ingredient 100:1 to 1:100 50:1 to 1:50 20:1to 1:20 10:1 to 1:10 5:1 to 1:5 3:1 to 1:3 2:1 to 1:2 1:1

Weight ratios of a molecule of Formula A, Formula One, Formula Two orFormula Three to an active ingredient may also be depicted as X:Y;wherein X is the parts by weight of a molecule of Formula A, FormulaOne, Formula Two or Formula Three and Y is the parts by weight of activeingredient. The numerical range of the parts by weight for X is 0<X≤100and the parts by weight for Y is 0<Y≤100 and is shown graphically inTable B. By way of non-limiting example, the weight ratio of a moleculeof Formula A, Formula One, Formula Two or Formula Three to an activeingredient may be 20:1.

Ranges of weight ratios of a molecule of Formula A, Formula One, FormulaTwo or Formula Three to an active ingredient may be depicted as X₁:Y₁ toX₂:Y₂, wherein X and Y are defined as above.

TABLE B active ingredient 100 X, Y X, Y X, Y (Y) Parts by weight 50 X, YX, Y X, Y X, Y X, Y 20 X, Y X, Y X, Y X, Y X, Y 15 X, Y X, Y X, Y X, YX, Y 10 X, Y X, Y 5 X, Y X, Y X, Y X, Y 3 X, Y X, Y X, Y X, Y X, Y X, YX, Y 2 X, Y X, Y X, Y X, Y X, Y 1 X, Y X, Y X, Y X, Y X, Y X, Y X, Y X,Y X, Y 1 2 3 5 10 15 20 50 100 molecule of Formula A, Formula One,Formula Two or Formula Three (X) Parts by weight

In one embodiment, the range of weight ratios may be X₁:Y₁ to X₂:Y₂,wherein X₁>Y₁ and X₂<Y₂. By way of non-limiting example, the range of aweight ratio of a molecule of Formula A, Formula One, Formula Two orFormula Three to an active ingredient may be between 3:1 and 1:3,inclusive of the endpoints.

In another embodiment, the range of weight ratios may be X₁:Y₁ to X₂:Y₂,wherein X₁>Y₁ and X₂>Y₂. By way of non-limiting example, the range ofweight ratio of a molecule of Formula A, Formula One, Formula Two orFormula Three to an active ingredient may be between 15:1 and 3:1,inclusive of the endpoints.

In another embodiment, the range of weight ratios may be X₁:Y₁ to X₂:Y₂,wherein X₁<Y₁ and X₂<Y₂. By way of non-limiting example, the range ofweight ratios of a molecule of Formula A, Formula One, Formula Two orFormula Three to an active ingredient may be between about 1:3 and about1:20, inclusive of the endpoints.

It is envisioned that certain weight ratios of a molecule of Formula A,Formula One, Formula Two or Formula Three to an active ingredient, aspresented in Table A and B, may be synergistic.

EXAMPLES

The examples are for illustration purposes and are not to be construedas limiting the invention disclosed in this document to only theembodiments disclosed in these examples.

Starting materials, reagents and solvents which are obtained fromcommercial sources are used without further purification. Anhydroussolvents are purchased as Sure/Seal™ from Aldrich and are used asreceived. Melting points are obtained on a Thomas Hoover Unimeltcapillary melting point apparatus or an OptiMelt Automated Melting PointSystem from Sanford Research Systems and are uncorrected. Examples using“room temperature” were conducted in climate controlled laboratorieswith temperatures ranging from about 20° C. to about 24° C. Moleculesare given their known names, named according to naming programs withinISIS Draw, ChemDraw, or ACD Name Pro. If such programs are unable toname a molecule, such molecule is named using conventional naming rules.¹H nuclear magnetic resonance (NMR) spectral data are in parts permillion (ppm, δ) and were recorded at 300, 400, or 500; ¹³C NMR spectraldata are in ppm (δ) and were recorded at 75, 100, or 150 MHz; and ¹⁹FNMR spectral data are in ppm (δ) and were recorded at 376 MHz, unlessotherwise stated.

Example 1: Preparation of1-(4-(perfluoroethoxy)phenyl)-3-(4-vinylphenyl)-1H-1,2,4-triazole (C1)

The title compound was prepared as in Fischer, L. G. et al., U. S.Patent Application Publication 2014/0274688 from4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde(prepared as in Crouse, G. et al., PCT International Application WO2009/102736 A1, 1.5 g, 3.9 mmol) and isolated as a white solid (895 mg,59%): mp 141-143° C.; ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), 8.19-8.13(m, 2H), 7.86-7.77 (m, 2H), 7.58-7.46 (m, 2H), 7.44-7.35 (m, 2H), 6.78(dd, J=17.6, 10.9 Hz, 1H), 5.84 (dd, J=17.6, 0.8 Hz, 1H), 5.32 (dd,J=10.8, 0.8 Hz, 1H); ¹⁹F NMR (376 MHz, CDCl₃) δ−85.90, −87.84; ESIMS m/z382 ([M+H]⁺).

Example 2: Preparation of2-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol(C2)

To 1-(4-(perfluoroethoxy)phenyl)-3-(4-vinylphenyl)-1H-1,2,4-triazole(C1; 896 milligrams (mg), 2.35 mmol) was dissolved in THF (15milliliters (mL)). 9-Borabicyclo[3.3.1]nonane (9-BBN; 9.4 mL, 4.7 mmol)was added, and the reaction mixture was stirred at room temperature for5 hours (h). 2 Normal (N) Sodium hydroxide (NaOH; 2.35 mL, 4.7 mmol) and30% hydrogen peroxide (0.6 mL, 5.9 mmol) were added sequentially. Aslight exotherm was observed. The bright yellow solution was stirred atroom temperature and turned pale over 2 h. After 2 h, the mixture wasdiluted with water and extracted with ethyl acetate. The organicextracts were dried over sodium sulfate, filtered, and concentrated togive a clear oil. The oil was loaded onto a Celite® cartridge withdichloromethane (DCM). Purification by flash chromatography (0-100%ethyl acetate/hexanes) provided the title compound as a white solid (223mg, 23%): mp 91-96° C.; ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H),8.16-8.11 (m, 2H), 7.83-7.78 (m, 2H), 7.40 (d, J=8.8 Hz, 2H), 7.36 (d,J=8.2 Hz, 2H), 3.92 (q, J=6.4 Hz, 2H), 2.95 (t, J=6.5 Hz, 2H), 1.40 (t,J=5.9 Hz, 1H); ¹⁹F NMR (376 MHz, CDCl₃) δ−85.90, −87.84; ESIMS m/z 400([M+H]⁺).

Example 3: Preparation of(E)-N-((dimethylamino)methylene)-4-methoxybenzamide (C3)

4-Methoxybenzamide (10 g, 66 mmol) in N,N-dimethylformamide dimethylacetal (DMF-DMA; 35 mL) was heated at 90° C. for 2 h. The reactionmixture was cooled, diluted with diethyl ether and ethyl acetate, andwashed twice with water. The organic layer was dried over sodiumsulfate, filtered, and concentrated. The title compound was isolated asa white solid (11.9 g, 86%): mp 92-93° C.; ¹H NMR (400 MHz, DMSO-d₆) δ8.56 (s, 1H), 8.13-8.07 (m, 2H), 7.00-6.92 (m, 2H), 3.81 (s, 3H), 3.18(s, 3H), 3.12 (s, 3H); ¹³C NMR (101 MHz, DMSO-d₆) δ 175.23, 162.07,160.40, 131.20, 129.43, 113.18, 55.25, 40.76, 34.82.

Example 4: Preparation of 3-(4-methoxyphenyl)-1H-1,2,4-triazole (C4)

To (E)-N-((dimethylamino)methylene)-4-methoxybenzamide (C3; 11.9 g, 57.5mmol) in acetic acid (75 mL) was added hydrazine monohydrate (2.7 mL, 87mmol). The reaction mixture was heated at 100° C. for 1.5 h. Thereaction mixture was cooled, diluted with water, and allowed to sit atroom temperature for 3 days. The white precipitate was filtered anddried. The title compound was isolated as a white solid (7.50 g, 74%):mp 188-189.5° C.; ¹H NMR (400 MHz, DMSO-d₆) δ 14.09 (s, 1H), 8.35 (s,1H), 8.12-7.79 (m, 2H), 7.05 (d, J=8.6 Hz, 2H), 3.81 (s, 3H); EIMS m/z175.

Example 5: Preparation of3-(4-methoxyphenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole(C5)

3-(4-Methoxyphenyl)-1H-1,2,4-triazole (C4; 4.47 g, 256 mmol),1-iodo-4-(trifluoromethoxy)benzene (10.3 g, 36 mmol), cesium carbonate(22.4 g, 69 mmol), copper(I) iodide (1.98 g, 10.4 mmol), and8-hydroxyquinoline (1.49 g, 10.3 mmol) in N,N-dimethylformamide (DMF;160 mL) and water (16 mL) was heated at 150° C. for 6 h. The reactionmixture was cooled to room temperature overnight. The reaction wasquenched with water and ammonium hydroxide, and the mixture wasextracted with diethyl ether. The emulsion was filtered to remove coppersolids, and the mixture was extracted once more with diethyl ether. Thecombined organic extracts were washed with water, dried over sodiumsulfate, filtered, and concentrated. Purification of the resultingconcentrate by flash chromatography (0-50% ethyl acetate/hexanes)provided the title compound as a white solid (4.58 g, 53%): mp99.5-100.5° C.; ¹H NMR (400 MHz, CDCl₃) δ 8.53 (s, 1H), 8.18-8.07 (m,2H), 7.84-7.73 (m, 2H), 7.38 (dd, J=9.0, 0.7 Hz, 2H), 7.08-6.96 (m, 2H),3.88 (s, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ−58.04; EIMS m/z 335.

Example 6: Preparation of4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenol (C6)

To 3-(4-methoxyphenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole(C5; 4.57 g, 13.6 mmol) in DCM (45 mL) at 0° C. was added borontribromide (1 molar (M) solution in DCM; 41 mL, 41 mmol) in portionsover 15 minutes (min). The reaction mixture was stirred at 0° C. for 2.5h. The reaction mixture was diluted with DCM and water, cooled in an icebath, and brought to pH 7 by the slow addition of a saturated aqueoussodium bicarbonate solution. The organic layer was separated, and theaqueous layer was extracted twice with ethyl acetate. The combinedorganic layers were dried over sodium sulfate, filtered, andconcentrated. The resultant material was adsorbed onto silica gel.Purification by flash chromatography (0-100% ethyl acetate/hexanes)provided the title compound as a white solid (3.99 g, 91%): mp 182-184°C.; ¹H NMR (400 MHz, DMSO-d₆) δ 9.84 (s, 1H), 9.32 (s, 1H), 8.09-7.98(m, 2H), 7.98-7.87 (m, 2H), 7.61 (d, J=8.3 Hz, 2H), 6.94-6.83 (m, 2H);¹⁹F NMR (376 MHz, DMSO-d₆) δ−56.98; ESIMS m/z 322 ([M+H]⁺).

Example 7: Preparation of1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-one(C7)

A solution of3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole(prepared as in Fischer, L. G. et al., U. S. Patent ApplicationPublication 2014/0274688; 12.3 g, 32.0 mmol), potassium phosphate (20.4g, 96 mmol), water (0.692 g, 38.4 mmol), copper(I) iodide (0.61 g, 3.2mmol), and pentane-2,4-dione (9.62 g, 96 mmol) in DMSO (100 mL) wasdegassed under nitrogen for 30 min. The reaction mixture was heated at90° C. for 24 h. The reaction mixture was cooled, diluted with water(150 mL), and extracted with diethyl ether (2×150 mL). The combinedorganic layers were washed with water, dried over sodium sulfate, andconcentrated. Purification by flash chromatography (0-70% ethylacetate/hexanes) provided the title compound as an off-white solid (7.15g, 60%): mp 91-95° C.; ¹H NMR (400 MHz, CDCl₃) δ 8.58 (s, 1H), 8.17 (d,J=7.9 Hz, 2H), 7.84-7.75 (m, 2H), 7.44-7.37 (m, 2H), 7.33 (d, J=7.8 Hz,2H), 3.77 (s, 2H), 2.19 (s, 3H); ESIMS m/z 362 ([M+H]⁺).

Example 8: Preparation of1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-ol(C8)

To1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-one(C7; 3.74 g, 10.4 mmol) in ethanol (150 mL) was added sodium borohydride(0.78 g, 20.7 mmol). The reaction mixture was stirred at roomtemperature for 2 h. The solution was poured onto water and extractedwith ethyl acetate. The organic layers were dried over sodium sulfateand concentrated. The title compound was isolated as a beige solid (3.55g, 93%): mp 72-80° C.; ¹H NMR (400 MHz, CDCl₃) δ 8.56 (s, 1H), 8.18-8.09(m, 2H), 7.86-7.75 (m, 2H), 7.39 (dt, J=8.0, 1.0 Hz, 2H), 7.34 (d, J=8.2Hz, 2H), 4.10 (dd, J=14.0, 7.0 Hz, 1H), 2.94-2.65 (m, 2H), 1.54 (s, 1H),1.28 (d, J=6.2 Hz, 3H); ¹³C NMR (101 MHz, CDCl₃) δ 163.89, 153.06,141.95, 140.78, 136.05, 130.24, 129.14, 127.25, 126.77, 122.87, 121.66,69.31, 46.14, 23.36; ESIMS m/z 364 ([M+H]⁺).

Example 9: Preparation of3-(4-(oxiran-2-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole(C9)

To a solution of1-(4-(trifluoromethoxy)phenyl)-3-(4-vinylphenyl)-1H-1,2,4-triazole(prepared as in Fischer, L. G. et al., U. S. Patent ApplicationPublication 2014/0274688; 10 g, 30.2 mmol) in DCM (60 mL) was addedmeta-chloroperoxybenzoic acid (m-CPBA; 11.8 g, 45.3 mmol) portion wiseat 0° C., and the reaction mixture was warmed to room temperature for 4h. The reaction mixture was quenched with saturated aqueous sodiumbicarbonate and extracted with ethyl acetate (3×150 mL). The organiclayer was washed with water and brine, dried over anhydrous sodiumsulfate, filtered, and concentrated under reduced pressure. Purificationby column chromatography (15-20% ethyl acetate/petroleum ether) providedthe title compound as a pale yellow solid (7 g, 70%): ¹H NMR (300 MHz,CDCl₃) δ 8.60 (s, 1H), 8.18 (d, J=7.8 Hz, 2H), 7.80 (d, J=9.0 Hz, 2H),7.44-7.36 (m, 4H), 3.93-3.91 (m, 1H), 3.22-3.17 (m, 1H), 2.87-2.84 (m,1H); ESIMS m/z 348 ([M+H]⁺).

The following compound was prepared according to the procedure inExample 9.

3-(4-(Oxiran-2-yl)phenyl)-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazole(C10)

The title compound was prepared from intermediate C1 and was isolated asan off-white solid (5 g, 80%): ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H),8.18 (d, J=8.4 Hz, 2H), 7.82-7.79 (m, 2H), 7.44-7.38 (m, 4H), 3.96-3.91(m, 1H), 3.21-3.18 (m, 1H), 2.88-2.84 (m, 1H); ESIMS m/z 398 ([M+H]⁺).

Example 10: Preparation of2-fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol(C11)

To a solution of3-(4-(oxiran-2-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole(C9, 7 g, 20.2 mmol) in DCM (50 mL) was added pyridine hydrofluoride(HF-pyridine; 9 mL, 30.3 mmol) dropwise at 0° C., and the reactionmixture was stirred at room temperature for 4 h. The reaction mixturewas quenched with water and extracted with ethyl acetate (3×50 mL). Theorganic layer was washed with water and brine, dried over anhydroussodium sulfate, filtered, and concentrated under reduced pressure.Purification by column chromatography (15-20% ethyl acetate/petroleumether) provided the title compound as an off-white solid (5 g, 64%): mp126-128° C. ¹H NMR (400 MHz, DMSO-d₆) δ 9.40 (s, 1H), 8.13 (d, J=8.4 Hz,2H), 8.10-8.05 (m, 2H), 7.62 (d, J=8.0 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H),5.66-5.51 (m, 1H), 5.20 (t, J=6.0 Hz, 1H), 3.79-3.29 (m, 2H); ¹⁹F NMR(376 MHz, DMSO-d₆) δ−56.98, −183.38; ESIMS m/z 368 ([M+H]⁺).

The following compound was prepared according to the procedure inExample 10.

2-Fluoro-2-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol(C12)

The title compound was prepared from intermediate C10 and was isolatedas an off-white solid (5 g, 49%): ¹H NMR (400 MHz, DMSO-d₆) δ 9.41 (s,1H), 8.14-8.06 (m, 4H), 7.63 (d, J=9.2 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H),5.66-5.51 (m, 1H), 5.20 (t, J=5.6 Hz, 1H), 3.79-3.29 (m, 2H); ¹⁹F NMR(376 MHz, DMSO-d₆) δ−85.20, −86.89, −183.38; ESIMS m/z 418 ([M+H]⁺).

Example 11: Preparation of2-chloro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol(C13)

A solution of3-(4-(oxiran-2-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole(C9; 175 mg, 0.50 mmol), trichloroisocyanuric acid (59 mg, 0.25 mmol),and triphenylphosphine (198 mg, 0.76 mmol) in acetonitrile (4.9 mL) andwater (0.1 mL) was stirred at room temperature for 3 h. The reactionmixture was concentrated under a stream of nitrogen overnight. Theyellow oil was loaded onto a Celite® cartridge with DCM. Purification byflash chromatography (0-100% ethyl acetate/hexanes) provided the titlecompound as a white solid (114 mg, 58%): mp 135-137° C.; ¹H NMR (400MHz, CDCl₃) δ 8.57 (s, 1H), 8.24-8.18 (m, 2H), 7.84-7.76 (m, 2H),7.55-7.51 (m, 2H), 7.43-7.36 (m, 2H), 5.06 (dd, J=7.2, 5.7 Hz, 1H), 3.99(ddd, J=8.0, 5.9, 2.1 Hz, 2H), 2.12 (dd, J=7.8, 6.2 Hz, 1H); ¹⁹F NMR(376 MHz, CDCl₃) δ−58.03; ESIMS m/z 384 ([M+H]⁺).

Example 12: Preparation of3-(4-iodophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C14)

An oven-dried round bottomed flask was charged with3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole(prepared as in Fischer, L. G. et al., U. S. Patent ApplicationPublication 2014/0274688; 25.1 g, 65.2 mmol),(1R,2R)—N₁,N₂-dimethylcyclohexane-1,2-diamine (1.39 g, 9.8 mmol), sodiumiodide (20.0 g, 134 mmol), copper(I) iodide (1.24 g, 6.52 mmol), anddioxane (100 mL). The reaction mixture was heated at 100° C. After 24 h,additional sodium iodide (5.0 g) and copper(I) iodide (0.60 g) wereadded and the reaction mixture was heated another 24 h at 100° C. After24 h, additional (1R,2R)—N₁,N₂-dimethylcyclohexane-1,2-diamine (1.0 g),sodium iodide (5.5 g), and copper(I) iodide (1.0 g) were added. Thereaction mixture was heated at 100° C. for 24 h. The reaction mixturewas cooled, and the reaction quenched with saturated ammonium chlorideand ammonium hydroxide. The mixture was stirred for 1 h. The biphasicmixture was extracted twice with ethyl acetate. The organic layers weredried over sodium sulfate, filtered, and concentrated. The resultingsolid was adsorbed onto Celite®. Purification by reverse-phase flashchromatography (0-100% acetonitrile/water) provided the title compoundas an off-white fluffy solid (28.0 g, 99%): mp 107-108° C.; ¹H NMR (300MHz, CDCl₃) δ 8.56 (s, 1H), 7.97-7.89 (m, 2H), 7.87-7.76 (m, 4H), 7.39(dq, J=9.0, 1.0 Hz, 2H); ¹³C NMR (101 MHz, CDCl₃) δ 162.79, 148.51,141.62, 137.87, 135.46, 129.88, 128.22, 122.42, 121.26, 119.10, 95.94;¹⁹F NMR (376 MHz, CDCl₃) δ−58.03; HRMS-ESI (m/z) [M+H]⁺ calcd forC₁₅H₉F₃IN₃O, 430.9742; found, 430.9742.

Example 13: Preparation of ethyl2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetate(C15)

A dry round-bottomed flask was charged with3-(4-iodophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C14;2.60 g, 4.8 mmol), copper (0.92 g, 14.5 mmol), and dimethyl sulfoxide(DMSO; 8 mL). The flask was evacuated and backfilled with nitrogen.Ethyl 2-bromo-2,2-difluoroacetate (1.3 mL, 10.1 mmol) was added and thereaction mixture was heated at 60° C. for 24 h. The reaction mixture wascooled, and the reaction quenched with saturated ammonium chloride. Themixture was extracted with ethyl acetate. The organic layer was washedfour times with water, dried over sodium sulfate, filtered, andconcentrated. The brown oil was loaded onto a Celite® cartridge.Purification by flash chromatography (0-20% ethyl acetate/hexanes)provided the title compound as an off-white solid (1.72 g, 82%): mp51.5-53.2° C.; ¹H NMR (300 MHz, CDCl₃) δ 8.59 (s, 1H), 8.36-8.21 (m,2H), 7.87-7.78 (m, 2H), 7.78-7.64 (m, 2H), 7.40 (dt, J=8.0, 0.9 Hz, 2H),4.32 (q, J=7.2 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H); ¹⁹F NMR (376 MHz, CDCl₃)δ−58.02, −104.09; ESIMS m/z 428 ([M+H]⁺); HRMS-ESI (m/z) [M+H]⁺ calcdfor C₁₉H₁₄F₅N₃O₃, 427.0955; found, 427.0964.

Example 14: Preparation of2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide(C16)

To ethyl2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetate(C15; 0.81 g, 1.90 mmol) in methanol (19 ml) was added 2 M ammonia (7.6mL, 15.2 mmol). The reaction mixture was stirred at room temperature for30 min, then concentrated under a stream of nitrogen. The title compoundwas isolated as a white solid (770 mg, 100%): mp 218-226° C.; ¹H NMR(300 MHz, DMSO-d₆) δ 9.46 (s, 1H), 8.43 (s, 1H), 8.25 (d, J=8.1 Hz, 2H),8.12-8.06 (m, 3H), 7.74 (d, J=8.2 Hz, 2H), 7.64 (d, J=8.5 Hz, 2H); ¹³CNMR (126 MHz, DMSO-d₆) δ 165.78, 165.53, 165.29, 161.66, 147.74, 147.73,144.62, 136.06, 135.05, 134.85, 134.64, 126.78, 126.40, 123.06, 121.80,121.52, 119.48, 115.00; ¹⁹F NMR (471 MHz, DMSO-d₆) δ−56.95, −101.91;ESIMS m/z 399 ([M+H]⁺); HRMS-ESI (m/z) [M+H]⁺ calcd for C₁₇H₁₁F₅N₄O₂,398.0802, found, 398.0806.

Example 15: Preparation of2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol(C17) and2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-amine(C18)

2,2-Difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-acetamide(C16; 109 mg, 0.27 mmol) in 1 M borane-THF complex in THE (1.1 mL, 1.1mmol) was heated at 60° C. for 3 days. 2 N Hydrochloric acid (HCl) wasadded to the mixture, and the reaction mixture was stirred at 50° C. for2 h. The mixture was cooled and made basic with 50% weight per weight(w/w) NaOH. The solution was diluted with water and extracted twice withethyl acetate. The organic extracts were dried over sodium sulfate,filtered, and concentrated. The residue was purified by reverse-phaseflash chromatography (0-100% acetonitrile/water) to provide a mixture ofthe title compounds. C17: ESIMS m z 386 ([M+H]⁺); C18: ESIMS m/z 385([M+H]⁺).

Example 16: Preparation of2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(2,5-dioxopyrrolidin-1-yl) carbonate (C19) and 2,5-dioxopyrrolidin-1-yl(2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl)carbamate(C20)

To a mixture of2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanol(C17) and2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine(C18; 320 mg, ˜0.92 mmol) were added bis(2,5-dioxopyrrolidin-1-yl)carbonate (282 mg, 1.1 mmol), acetonitrile (3 mL), and pyridine (0.09mL, 1.1 mmol). The reaction mixture was stirred at room temperature for5 h and loaded directly onto a Celite® cartridge with acetonitrile. Thecartridge was dried in a vacuum oven overnight. Purification byreverse-phase flash chromatography (0-100% acetonitrile/water) providedthe title carbonate (25 mg, 43%) and the title carbamate (14 mg, 74%purity).

Carbonate C19: ¹H NMR (400 MHz, CDCl₃) δ 8.59 (s, 1H), 8.31 (d, J=8.2Hz, 2H), 7.84-7.79 (m, 2H), 7.65 (d, J=8.3 Hz, 2H), 7.43-7.38 (m, 2H),4.69 (t, J=12.3 Hz, 2H), 2.83 (s, 4H); ¹⁹F NMR (376 MHz, CDCl₃) δ−58.02,−104.97; ESIMS m/z 527 ([M+H]⁺).

Example 17: Preparation of 2,5-dioxopyrrolidin-1-yl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)carbonate (C21)

To2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol(prepared as in Fischer, L. G. et al., U. S. Patent ApplicationPublication 2014/0274688; 320 mg, 0.92 mmol) andbis(2,5-dioxopyrrolidin-1-yl) carbonate (282 mg, 1.1 mmol) inacetonitrile (3 mL) was added pyridine (0.09 mL, 1.1 mmol), and thereaction mixture was stirred at room temperature for 4 h. The reactionmixture was concentrated under nitrogen and loaded onto a Celite®cartridge with DCM. Purification by flash chromatography (0-100% ethylacetate/hexanes) provided the title compound as a clear oil (498 mg,100%): ¹H NMR (400 MHz, CDCl₃) δ 8.62 (s, 1H), 8.17-8.12 (m, 2H),7.85-7.78 (m, 2H), 7.43-7.31 (m, 4H), 4.55 (t, J=7.1 Hz, 2H), 3.13 (t,J=7.1 Hz, 2H), 2.84 (s, 4H); ¹⁹F NMR (376 MHz, CDCl₃) δ−58.02; ESIMS m/z491 ([M+H]⁺).

The following compounds were prepared according to the procedure inExample 17.

2,5-Dioxopyrrolidin-1-yl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)carbonate (C22)

The title compound was prepared from compound C6 and isolated as a clearoil (56 mg, 28%): ¹H NMR (400 MHz, CDCl₃) δ 8.70 (d, J=3.0 Hz, 1H),8.27-8.19 (m, 2H), 7.86-7.77 (m, 2H), 7.45-7.37 (m, 4H), 2.90 (s, 4H);¹⁹F NMR (376 MHz, CDCl₃) δ−58.01; ESIMS m/z 463 ([M+H]⁺).

2,5-Dioxopyrrolidin-1-yl(1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-yl)carbonate (C23)

The title compound was prepared from compound C8 and isolated as a clearoil (97 mg, 98%); ESIMS m/z 505 ([M+H]⁺).

Example 18: Preparation of4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A1)

2,5-Dioxopyrrolidin-1-yl4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethylcarbonate (C21; 21.5 mg, 0.044 mmol),2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (prepared as inFischer, L. G. et al., U. S. Patent Application Publication2014/0274688; 16 mg, 0.064 mmol), and sodium bicarbonate (14 mg, 0.17mmol) in DCM (0.2 mL) and water (0.1 mL) were stirred at roomtemperature overnight. The reaction mixture was diluted with DCM andfiltered through a phase separator directly onto a Celite® cartridge.Purification by flash chromatography (0-100% ethyl acetate/B, whereB=1:1 DCM/hexanes) provided the title compound as a white solid (18 mg,65%).

The following compounds were prepared according to the procedure inExample 18.

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A2)

The title compound was prepared from compound C21 and2-imino-3-(2-isopropylphenyl)thiazolidin-4-one (prepared as in Baum, E.W. et al., PCT International Application WO 2016/033025 A1) and isolatedas a white solid (51 mg, 80%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl(Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A3)

The title compound was prepared from compound C22 and2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (prepared as inFischer, L. G. et al., U. S. Patent Application Publication2014/0274688) and isolated as a white foamy solid (30 mg, 38%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-ethoxyphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A5)

The title compound was prepared from compound C21 and3-(2-ethoxyphenyl)-2-iminothiazolidin-4-one (prepared as in Baum, E. W.et al., PCT International Application WO 2018/067764) and isolated as ayellow oil (28 mg, 31%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-butylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A6)

The title compound was prepared from compounds C21 and C44 and isolatedas a cream solid (45 mg, 69%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-(2-cyclopropylethyl)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A7)

The title compound was prepared from compounds C21 and C45 and isolatedas a cream solid (43 mg, 61%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(4-oxo-3-(2-(3,3,3-trifluoropropyl)phenyl)thiazolidin-2-ylidene)carbamate(A8)

The title compound was prepared from compounds C21 and C47 and isolatedas a cream solid (42 mg, 59%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl((Z)-4-oxo-3-(2-((E)-3,3,3-trifluoroprop-1-en-1-yl)phenyl)thiazolidin-2-ylidene)carbamate(A9)

The title compound was prepared from compounds C21 and C46 and isolatedas a white solid (43 mg, 62%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(4-methoxy-2-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A10)

The title compound was prepared from intermediates C21 and2-imino-3-(4-methoxy-2-methylphenyl)thiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as a white solid (52 mg, 56%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-fluoro-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A11)

The title compound was prepared from compound C21 and3-(2-fluoro-5-methylphenyl)-2-iminothiazolidin-4-one (prepared as inGiampietro, N. C. et al., PCT International Application WO 2017/040194A1) and isolated as a white solid (47 mg, 76%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-chloro-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A12)

The title compound was prepared from compound C21 and3-(2-chloro-5-methylphenyl)-2-iminothiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as a white solid (48 mg, 74%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-methoxy-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A13)

The title compound was prepared from compound C21 and2-imino-3-(2-methoxy-5-methylphenyl)thiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as a tan solid (40 mg, 60%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(5-methyl-2-(trifluoromethyl)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A14)

The title compound was prepared from compound C21 and2-imino-3-(5-methyl-2-(trifluoromethyl)phenyl)thiazolidin-4-one(prepared as in Giampietro, N. C. et al., PCT International ApplicationWO 2017/040742 A1) and isolated as a white solid (19 mg, 28%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(5-methyl-2-propylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A15)

The title compound was prepared from compound C21 and2-imino-3-(5-methyl-2-propylphenyl)thiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as a white solid (45 mg, 68%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-ethoxy-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A16)

The title compound was prepared from compound C21 and3-(2-ethoxy-5-methylphenyl)-2-iminothiazolidin-4-one (prepared as inGiampietro, N. C. et al., PCT International Application WO 2017/040742A1) and isolated as a tan solid (33 mg, 49%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(4-fluoro-2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A17)

The title compound was prepared from compound C21 and3-(4-fluoro-2-isopropyl-5-methylphenyl)-2-iminothiazolidin-4-one(prepared as in Giampietro, N. C. et al., PCT International ApplicationWO 2017/040742 A1) and isolated as a white solid (76 mg, 79%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-chloro-4,5-dimethylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A18)

The title compound was prepared from compounds C21 and C48 and isolatedas a cream solid (50 mg, 75%).

1-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-yl(Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A19)

The title compound was prepared from compound C23 and2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (prepared as inFischer, L. G. et al., U. S. Patent Application Publication 2014/0274688and isolated as a tan solid (50 mg, 41%).

Example 19: Preparation of4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-(methoxymethyl)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A27)

To2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol(prepared as in Fischer, L. G. et al., U. S. Patent ApplicationPublication 2014/0274688; 50 mg, 0.14 mmol) andbis(2,5-dioxopyrrolidin-1-yl) carbonate (48 mg, 0.19 mmol) inacetonitrile (0.72 mL) was added pyridine (0.045 mL, 0.57 mmol). Thereaction was stirred at room temperature overnight. The reaction mixturewas concentrated under a stream of nitrogen to provide C21.2-Imino-3-(2-(methoxymethyl)phenyl)thiazolidin-4-one (C49; 34 mg, 0.14mmol), DCM (0.5 mL), water (0.25 mL), and sodium bicarbonate (120 mg,1.43 mmol) were added. The reaction mixture was stirred at roomtemperature overnight and filtered through a phase separator rinsingwith DCM directly onto a Celite® cartridge. Purification by flashchromatography (0-100% ethyl acetate/hexanes) provided the titlecompound as a yellow oil (34 mg, 37%).

The following compounds were prepared according to the procedure inExample 19.

2-Fluoro-2-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A24)

The title compound was prepared from compound C12 and2-imino-3-(2-isopropylphenyl)thiazolidin-4-one (prepared as in Baum, E.W. et al., PCT International Application WO 2016/033025 A1) and isolatedas a yellow oil (77 mg, 90%).

2-Fluoro-2-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(5-chloro-2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A25)

The title compound was prepared from compound C12 and3-(5-chloro-2-isopropylphenyl)-2-iminothiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as an orange oily solid (32 mg, 36%).

2-Fluoro-2-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A26)

The title compound was prepared from compound C12 and2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (prepared as inFischer, L. G. et al., U. S. Patent Application Publication2014/0274688) and isolated as a white solid (19 mg, 22%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-(sec-butyl)-5-methoxyphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A28)

The title compound was prepared from compounds C21 and C50 and isolatedas a white solid (83 mg, 87%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(5-chloro-2-(trifluoromethoxy)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A29)

The title compound was prepared from compounds C21 and C51 and isolatedas a white solid (63 mg, 63%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(5-chloro-2-(2,2,2-trifluoroethoxy)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A30)

The title compound was prepared from compounds C21 and C52 and isolatedas a yellow solid (77 mg, 75%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(5-methyl-2-(2,2,2-trifluoroethoxy)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A31)

The title compound was prepared from compounds C21 and2-imino-3-(5-methyl-2-(2,2,2-trifluoroethoxy)phenyl)thiazolidin-4-one(prepared as in Giampietro, N. C. et al., PCT International ApplicationWO 2017/040742 A1) and isolated as a white solid (94 mg, 92%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-ethyl-6-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A32)

The title compound was prepared from compounds C21 and3-(2-ethyl-6-methylphenyl)-2-iminothiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as a white solid (87 mg, 95%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(4-oxo-3-(5,6,7,8-tetrahydronaphthalen-1-yl)thiazolidin-2-ylidene)carbamate(A33)

The title compound was prepared from compounds C21 and C53 and isolatedas a tan solid (65 mg, 69%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A34)

The title compound was prepared from compound C11 and2-imino-3-(2-isopropylphenyl)thiazolidin-4-one (prepared as in Baum, E.W. et al., PCT International Application WO 2016/033025 A1) and isolatedas a clear oil (22 mg, 25%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-(sec-butoxy)-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A35)

The title compound was prepared from compound C21 and3-(2-(sec-butoxy)-5-methylphenyl)-2-iminothiazolidin-4-one (prepared asin Giampietro, N. C. et al., PCT International Application WO2017/040742 A1) and isolated as an off-white solid (59 mg, 62%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(5-chloro-2-(trifluoromethoxy)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A36)

The title compound was prepared from compounds C11 and C51 and isolatedas an orange oily solid (53 mg, 54%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(4-methoxy-2-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A37)

The title compound was prepared from compound C11 and2-imino-3-(4-methoxy-2-methylphenyl)thiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as an off-white solid (24 mg, 27%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-chloro-4,5-dimethylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A38)

The title compound was prepared from compounds C11 and C48 and isolatedas a tan solid (61 mg, 66%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(4-oxo-3-(5,6,7,8-tetrahydronaphthalen-1-yl)thiazolidin-2-ylidene)carbamate(A39)

The title compound was prepared from compounds C11 and C53 and isolatedas an orange solid (79 mg, 86%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-ethoxyphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A40)

The title compound was prepared from compound C11 and3-(2-ethoxyphenyl)-2-iminothiazolidin-4-one (prepared as in Baum, E. W.et al., PCT International Application WO 2018/067764) and isolated as ayellow oil (5.5 mg, 6%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-(sec-butoxy)-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A41)

The title compound was prepared from compound C11 and3-(2-(sec-butoxy)-5-methylphenyl)-2-iminothiazolidin-4-one (prepared asin Giampietro, N. C. et al., PCT International Application WO2017/040742 A1) and isolated as an orange oily solid (40 mg, 42%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-ethyl-6-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A42)

The title compound was prepared from compound C11 and3-(2-ethyl-6-methylphenyl)-2-iminothiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as a white solid (29 mg, 33%).

4-(1-(4-(Perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(5-chloro-2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A43)

The title compound was prepared from compound C2 and3-(5-chloro-2-isopropylphenyl)-2-iminothiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as an orange oily solid (42 mg, 38%).

4-(1-(4-(Perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A44)

The title compound was prepared from compound C2 and2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (prepared as inFischer, L. G. et al., U. S. Patent Application Publication2014/0274688; 16 mg, 0.064 mmol) and isolated as a tan solid (70 mg,66%).

4-(1-(4-(Perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A45)

The title compound was prepared from compound C2 and2-imino-3-(2-isopropylphenyl)thiazolidin-4-one (prepared as in Baum, E.W. et al., PCT International Application WO 2016/033025 A1) and isolatedas a white solid (53 mg, 51%).

2-Chloro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A46)

The title compound was prepared from compound C13 and2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (prepared as inFischer, L. G. et al., U. S. Patent Application Publication2014/0274688) and isolated as a yellow oil (27 mg, 79%).

2-Chloro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A47)

The title compound was prepared from compound C13 and2-imino-3-(2-isopropylphenyl)thiazolidin-4-one (prepared as in Baum, E.W. et al., PCT International Application WO 2016/033025 A1) and isolatedas a white sticky solid (38 mg, 54%).

2-Chloro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(5-chloro-2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A48)

The title compound was prepared from compound C13 and3-(5-chloro-2-isopropylphenyl)-2-iminothiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as a clear oil (34 mg, 47%).

1-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-yl(Z)-(3-(2-(sec-butoxy)-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A49)

The title compound was prepared from compound C23 and3-(2-(sec-butoxy)-5-methylphenyl)-2-iminothiazolidin-4-one (prepared asin Giampietro, N. C. et al., PCT International Application WO2017/040742 A1) and isolated as a yellow oil (12 mg, 11%).

1-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-yl(Z)-(3-(2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A50)

The title compound was prepared from compound C23 and2-imino-3-(2-isopropylphenyl)thiazolidin-4-one (prepared as in Baum, E.W. et al., PCT International Application WO 2016/033025 A1) and isolatedas a tan oily foam (28 mg, 27%).

1-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-yl(Z)-(3-(2-ethoxyphenyl)-4-oxothiazolidin-2-ylidene)carbamate (A51)

The title compound was prepared from compound C23 and3-(2-ethoxyphenyl)-2-iminothiazolidin-4-one (prepared as in Baum, E. W.et al., PCT International Application WO 2018/067764) and isolated as ayellow oil (17 mg, 16%).

1-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-yl(Z)-(3-(2-ethyl-6-methylphenyl)-4-oxothiazolidin-2-ylidene carbamate(A52)

The title compound was prepared from compound C23 and3-(2-ethyl-6-methylphenyl)-2-iminothiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as an orange oily foam (42 mg, 40%).

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl(Z)-(3-(2-isopropyl-5-methylphenyl)thiazol-2(3H)-ylidene)carbamate (A53)

The title compound was prepared from intermediates C21 and3-(2-isopropyl-5-methylphenyl)thiazol-2(3H)-imine (prepared as inGiampietro, N. C. et al., PCT International Application WO 2017/040742A1) and isolated as a white solid (76 mg, 86%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-isopropyl-5-methylphenyl)thiazol-2(3H)-ylidene)carbamate (A54)

The title compound was prepared from compound C11 and3-(2-isopropyl-5-methylphenyl)thiazol-2(3H)-imine (prepared as inGiampietro, N. C. et al., PCT International Application WO 2017/040742A1) and isolated as a clear oil (56 mg, 64%).

1-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-yl(Z)-(3-(2-isopropyl-5-methylphenyl)thiazol-2(3H)-ylidene)carbamate (A55)

The title compound was prepared from intermediates C23 and3-(2-isopropyl-5-methylphenyl)thiazol-2(3H)-imine (prepared as inGiampietro, N. C. et al., PCT International Application WO 2017/040742A1) and isolated as a white solid (44 mg, 41%).

Example 20: Preparation of2-fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A20)

Bis(2,5-dioxopyrrolidin-1-yl) carbonate (42 mg, 0.16 mmol) was added to2-fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol(C11, 50 mg, 0.14 mmol) and triethylamine (0.02 mL, 0.14 mmol) in DCM (1mL), and the reaction mixture was stirred at 23° C. overnight.2-Imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (prepared as inFischer, L. G. et al., U. S. Patent Application Publication2014/0274688; 34 mg, 0.14 mmol) was added, and the reaction mixture wasstirred at 23° C. overnight. The reaction mixture was filtered through aphase separator, rinsing with DCM. The filtrate was concentrated ontosilica gel. Purification by flash chromatography (silica/ethylacetate/DCM-hexanes) yielded the title compound as an off-white solid(70 mg, 76%).

The following compounds were prepared according to the procedure inExample 20.

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(5-methyl-2-(2,2,2-trifluoroethoxy)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A21)

The title compound was prepared from intermediates C11 and2-imino-3-(5-methyl-2-(2,2,2-trifluoroethoxy)phenyl)thiazolidin-4-one(prepared as in Giampietro, N. C. et al., PCT International ApplicationWO 2017/040742 A1) and isolated as a white foam (73 mg, 73%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(5-chloro-2-(2,2,2-trifluoroethoxy)phenyl)-4-oxothiazolidin-2-ylidene)carbamate(A22)

The title compound was prepared from compounds C11 and C52 and isolatedas a white foam (56 mg, 54%).

2-Fluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(5-chloro-2-isopropylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A23)

The title compound was prepared from compound C11 and3-(5-chloro-2-isopropylphenyl)-2-iminothiazolidin-4-one (prepared as inBaum, E. W. et al., PCT International Application WO 2016/033025 A1) andisolated as a white foam (60 mg, 63%).

Example 21: Preparation of2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate(A4)

A mixture of2,2-difluoro-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethyl(2,5-dioxopyrrolidin-1-yl) carbonate (C19; 22 mg, 0.042 mmol),2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (prepared as inFischer, L. G. et al., U. S. Patent Application Publication2014/0274688; 20 mg, 0.081 mmol), and sodium bicarbonate (16 mg, 0.19mmol) in DCM (0.5 mL) and water (0.1 mL) was stirred at room temperaturefor 3 h. The reaction mixture was filtered through a phase separatordirectly onto a Celite® cartridge, rinsing with DCM. Purification byflash chromatography (0-100% ethyl acetate/B, where B=1:1 DCM/hexanes)provided impure product. Further purification by flash chromatography(0-40, 40-40, 40-100% ethyl acetate/hexanes) provided the title compoundas a white solid (21 mg, 75%).

Example 22: Preparation of (E)-1-(2-cyclopropylvinyl)-2-nitrobenzene(C24)

To a suspension of (cyclopropylmethyl)triphenylphosphonium bromide (3.57g, 8.99 mmol) in THE (24 mL) at 0° C. under nitrogen was added 1 Mpotassium tert-butoxide (18 mL, 18 mmol). The reaction mixture wasstirred at room temperature for 30 min. 2-Nitrobenzaldehyde (1.086 g,7.19 mmol) was added, and the reaction mixture was stirred at roomtemperature for 1 h. The reaction was quenched with 1 N HCl and pouredonto water. The mixture was extracted with ethyl acetate, and theorganic extracts were dried over sodium sulfate and concentrated.Purification by flash chromatography (0-20% ethyl acetate/hexanes)provided the title compound as a brown oil (482 mg, 32%): ¹H NMR (400MHz, CDCl₃) δ 7.85 (dd, J=8.1, 1.3 Hz, 1H), 7.62-7.41 (m, 2H), 7.35-7.26(m, 1H), 6.94 (d, J=15.6 Hz, 1H), 5.74 (dd, J=15.5, 9.2 Hz, 1H),1.71-1.58 (m, 1H), 0.97-0.80 (m, 2H), 0.65-0.43 (m, 2H); EIMS m/z 189.

Example 23: Preparation of 2-(2-cyclopropylethyl)aniline (C25)

A flask containing a degassed solution of(E)-1-(2-cyclopropylvinyl)-2-nitrobenzene (C24; 683 mg, 3.61 mmol) and10% palladium on carbon (154 mg, 1.44 mmol) was evacuated under vacuumand a balloon of hydrogen was added. The reaction mixture was stirred atroom temperature for 20 h. The solution was diluted with ethyl acetate,filtered through Celite®, and concentrated. Purification by flashchromatography (0-100% ethyl acetate/hexanes) provided the titlecompound as a yellow oil (220 mg, 37%): ¹H NMR (400 MHz, CDCl₃) δ7.13-6.97 (m, 2H), 6.73 (td, J=7.5, 1.3 Hz, 1H), 6.68 (dd, J=7.8, 1.2Hz, 1H), 3.64 (s, 2H), 2.68-2.54 (m, 2H), 1.58-1.46 (m, 2H), 0.81-0.67(m, 1H), 0.52-0.39 (m, 2H), 0.13-0.04 (m, 2H); ¹³C NMR (101 MHz, CDCl₃)δ 171.59, 144.53, 129.89, 127.27, 119.16, 115.94, 34.50, 31.62, 11.39,5.03; EIMS m/z 161.

Example 24: Preparation of (E)-2-(3,3,3-trifluoroprop-1-en-1-yl)aniline(C26)

To three separate 20 mL microwave vials were added potassium carbonate(1.704 g, 12.33 mmol), palladium(II) acetate (0.018 g, 0.082 mmol), and2-iodoaniline (0.9 g, 4.11 mmol). The vials were evacuated under vacuumand backfilled with nitrogen. The solids were dissolved in dry DMF (17mL) and stirred. 1,1,1-Trifluoro-3-iodopropane (0.482 mL, 4.11 mmol) wasadded via syringe. The reaction mixtures were heated in the microwave at200° C. for 1 h each. Each solution was diluted in hexanes and washedwith water. The hexanes layers were separated and combined. The aqueouslayer was extracted with ethyl acetate and then combined with thehexanes. All organic layers were dried and concentrated. Purification byflash chromatography (0-10% ethyl acetate/hexanes) provided the titlecompound as an orange solid (1.10 g, 42%): ¹H NMR (400 MHz, CDCl₃) δ7.32-7.26 (m, 1H), 7.23 (q, J=2.3 Hz, 1H), 7.21-7.15 (m, 1H), 6.87-6.74(m, 1H), 6.72 (dd, J=8.0, 1.1 Hz, 1H), 6.23-6.00 (m, 1H), 3.82 (s, 2H);¹⁹F NMR (376 MHz, CDCl₃) δ−63.13; EIMS m z 187.

Example 25: Preparation of 2-(3,3,3-trifluoropropyl)aniline (C27)

To a dry, evacuated 250 mL round-bottomed flask were added(E)-2-(3,3,3-trifluoroprop-1-en-1-yl)aniline (C26; 1.61 g, 8.60 mmol),methanol (30 mL), and palladium(II) hydroxide on carbon (0.483 g, 3.44mmol). The flask was evacuated and backfilled with nitrogen, thenevacuated and filled with hydrogen by balloon. The reaction mixture wasstirred at room temperature for 24 h. The solution was diluted in ethylacetate and filtered through Celite®. The filtrate was concentrated. Thetitle compound was isolated as an orange oil (1.45 g, 88%): ¹H NMR (400MHz, CDCl₃) δ 7.09 (td, J=7.7, 1.6 Hz, 1H), 7.04 (dd, J=7.5, 1.5 Hz,1H), 6.77 (td, J=7.4, 1.2 Hz, 1H), 6.71 (dd, J=7.9, 1.3 Hz, 1H), 3.62(s, 2H), 2.83-2.63 (m, 2H), 2.51-2.29 (m, 2H); ¹³C NMR (101 MHz, CDCl₃)δ 144.48, 129.68, 128.38, 125.97, 123.50, 119.57, 116.42, 33.15, 24.31;EIMS m/z 189.

Example 26: Preparation of 1-(methoxymethyl)-2-nitrobenzene (C28)

(2-Nitrophenyl)methanol (2 g, 13.1 mmol) was dissolved in THE (52 mL)and cooled to 0° C. To this mixture was added a 60% mineral oildispersion of sodium hydride (0.575 g, 14.4 mmol) in portions. Themixture was stirred at 0° C. for 30 min, and methyl iodide (2.45 mL,39.2 mmol) was added. The mixture was stirred an additional 90 min. Thereaction was quenched with a saturated aqueous ammonium chloridesolution and extracted with diethyl ether. The combined organic extractswere washed with brine, dried, and concentrated. Purification of theresulting yellow oil by flash chromatography (0-30% acetone/hexanes)provided the title compound as a clear yellow oil (1.45 g, 67%): ¹H NMR(400 MHz, CDCl₃) δ 8.07 (dd, J=8.2, 1.4 Hz, 1H), 7.79 (dd, J=7.8, 1.3Hz, 1H), 7.65 (td, J=7.6, 1.3 Hz, 1H), 7.47-7.41 (m, 1H), 4.85 (s, 2H),3.50 (s, 3H); EIMS m/z 166.

Example 27: Preparation of 2-(methoxymethyl)aniline (C29)

5% Palladium on carbon (0.926 g, 0.44 mmol) was added to1-(methoxymethyl)-2-nitrobenzene (C28; 1.45 g, 8.70 mmol) dissolved inethanol (17.4 mL) and ethyl acetate (17.4 mL). The flask was evacuatedand backfilled with a balloon of hydrogen. The reaction mixture wasstirred at room temperature overnight, filtered through Celite®, andconcentrated. Purification by flash chromatography (0-30% ethylacetate/hexanes) provided the title compound as a pale yellow oil (923mg, 77%): ¹H NMR (400 MHz, CDCl₃) δ 7.13 (td, J=7.6, 1.6 Hz, 1H),7.10-7.00 (m, 1H), 6.74-6.65 (m, 2H), 4.48 (s, 2H), 4.15 (s, 2H), 3.34(s, 3H); EIMS m/z 137.

Example 28: Preparation of(E)-1-(but-2-en-2-yl)-4-methoxy-2-nitrobenzene (C30)

To a suspension of 1-bromo-4-methoxy-2-nitrobenzene (2.8 g, 12.1 mmol)in DMF (40 mL), degassed with argon, were added(E)-but-2-en-2-yltributylstannane (prepared as in Org. Lett. 2013, 15,670-673; 4.5 g, 18.2 mmol), cesium fluoride (3.7 g, 24.2 mmol), andbis(triphenylphosphine)palladium(II) dichloride (Pd(PPh₃)₂Cl₂; 850 mg,1.2 mmol), and the reaction mixture was stirred at 80° C. for 16 h. Thereaction mixture was cooled to room temperature, poured into water andextracted with ethyl acetate (2×50 mL). The organic layer was washedwith brine, dried over sodium sulfate, filtered, and concentrated underreduced pressure. Purification by column chromatography (10-20% ethylacetate/petroleum ether) provided the title compound as a brown oil (1.5g, 60%): ¹H NMR (300 MHz, CDCl₃) δ 7.32 (d, J=2.7 Hz, 1H), 7.17 (d,J=8.4 Hz, 1H), 7.05 (dd, J=3.3, 8.4 Hz, 1H), 5.42 (q, J=1.5 Hz, 1H),3.85 (s, 3H), 1.90 (s, 3H), 1.73 (d, J=6.6 Hz, 3H); ESIMS m/z 208([M+H]⁺).

Example 29: Preparation of 2-(sec-butyl)-5-methoxyaniline (C31)

To a solution of (E)-1-(but-2-en-2-yl)-4-methoxy-2-nitrobenzene (C30;1.5 g, 7.25 mmol) in ethyl acetate (50 mL) was added 10% palladium oncarbon (1 g), and the reaction mixture was stirred under hydrogen gas(100 psi) in a Parr Shaker for 36 h. The reaction mixture was filteredthrough a pad of Celite®, washed with ethyl acetate, and the filtratewas concentrated under reduced pressure. The title compound was isolatedas a brown liquid (3 g, crude), which was used in the next step withoutpurification.

Example 30: Preparation of4-chloro-2-nitro-1-(2,2,2-trifluoroethoxy)benzene (C32)

To 4-chloro-2-nitrophenol (2 g, 11.5 mmol) in acetone (25 mL) were addedsequentially potassium carbonate (3.19 g, 23.1 mmol) and2,2,2-trifluoroethyl trifluoromethanesulfonate (2.5 mL, 17.3 mmol). Thereaction mixture was stirred overnight under nitrogen then warmed to 60°C. for 3 h. The mixture was cooled to room temperature and diluted withethyl acetate and water. The organic layer was separated and washed withbrine, dried over sodium sulfate, filtered and concentrated. The titlecompound was isolated as a red solid (2.8 g, 90%): mp 59-61° C.; ¹H NMR(400 MHz, CDCl₃) δ 7.90 (d, J=2.6 Hz, 1H), 7.55 (dd, J=8.9, 2.6 Hz, 1H),7.09 (d, J=8.9 Hz, 1H), 4.48 (q, J=7.9 Hz, 2H); ¹⁹F NMR (376 MHz, CDCl₃)δ−73.74; EIMS m/z 255.

Example 31: Preparation of 5-chloro-2-(2,2,2-trifluoroethoxy)aniline(C33)

To 4-chloro-2-nitro-1-(2,2,2-trifluoroethoxy)benzene (C32; 2.75 g, 10.8mmol) and ammonium chloride (0.288 g, 5.38 mmol) in ethanol (20 mL) andwater (5 mL) was added iron (3.00 g, 53.8 mmol). The reaction mixturewas heated to 70° C. for 3 h under nitrogen. The mixture was cooled toroom temperature and filtered through Celite®. The filtrate was dilutedwith ethyl acetate and water. The organic layer was separated and washedwith brine, dried over sodium sulfate, filtered and concentrated. Thetitle compound was isolated as a brown oil (2.63 g, 100%): ¹H NMR (400MHz, CDCl₃) δ 6.78-6.61 (m, 3H), 4.33 (q, J=8.1 Hz, 2H), 3.91 (s, 2H);¹⁹F NMR (376 MHz, CDCl₃) δ−74.13; ESIMS m/z 226 ([M+H]⁺).

Example 32: Preparation of N-(2-butylphenyl)-2-chloroacetamide (C34)

To a solution of commercially available 2-butylaniline (1 g, 6.70 mmol)in ethyl acetate (5 mL) in an ice bath was added sodium bicarbonate(1.12 g, 13.4 mmol) in portions. A solution of chloroacetyl chloride(0.64 mL, 8.0 mmol) in ethyl acetate (1 mL) was added. A whiteprecipitate formed and the suspension was stirred at room temperaturefor 30 min. The reaction mixture was diluted in ethyl acetate and washedwith water. The organic layer was dried over sodium sulfate andconcentrated. The title compound was isolated as a white solid (1.41 g,92%): ¹H NMR (400 MHz, CDCl₃) δ 8.32 (s, 1H), 7.91 (dd, J=8.0, 1.4 Hz,1H), 7.25-7.18 (m, 2H), 7.15 (dd, J=7.3, 1.3 Hz, 1H), 4.25 (s, 2H),2.70-2.48 (m, 2H), 1.67-1.50 (m, 2H), 1.48-1.32 (m, 2H), 0.95 (t, J=7.3Hz, 3H); ¹³C NMR (101 MHz, CDCl₃) δ 164.20, 134.61, 133.95, 130.26,127.35, 126.27, 123.18, 43.71, 32.54, 31.72, 23.05, 14.37; EIMS m/z 225.

The following compounds were prepared according to the procedure inExample 32.

2-Chloro-N-(2-(2-cyclopropylethyl)phenyl)acetamide (C35)

The title compound was prepared from compound C25 and isolated as a pinksolid (391 mg, 100% yield): ¹H NMR (400 MHz, CDCl₃) δ 8.39 (s, 1H), 7.85(dd, J=7.9, 1.3 Hz, 1H), 7.25-7.20 (m, 2H), 7.19-7.12 (m, 1H), 4.12 (s,2H), 2.79-2.66 (m, 2H), 1.51 (q, J=7.2 Hz, 2H), 0.76-0.65 (m, 1H),0.55-0.35 (m, 2H), 0.11-0.01 (m, 2H); ¹³C NMR (101 MHz, CDCl₃) δ 164.68,134.48, 134.12, 130.40, 127.33, 126.51, 123.56, 43.66, 41.02, 35.81,31.87, 11.07, 5.04; ESIMS m/z 238 ([M+H]⁺).

(E)-2-Chloro-N-(2-(3,3,3-trifluoroprop-1-en-1-yl)phenyl)acetamide (C36)

The title compound was prepared from compound C26 and isolated as apeach solid (777 mg, 91%): ¹H NMR (400 MHz, CDCl₃) δ 8.27 (s, 1H),7.79-7.73 (m, 1H), 7.50 (dd, J=7.8, 1.5 Hz, 1H), 7.43 (td, J=7.8, 1.6Hz, 1H), 7.32-7.26 (m, 2H), 6.21 (dq, J=16.0, 6.4 Hz, 1H), 4.26 (s, 2H);¹³C NMR (101 MHz, CDCl₃) δ 164.81, 134.63, 132.89, 131.16, 127.92,127.76, 127.24, 125.16, 120.39, 120.05, 43.45; ESIMS m/z 262 ([M−H]⁻).

2-Chloro-N-(2-(3,3,3-trifluoropropyl)phenyl)acetamide (C37)

The title compound was prepared from compound C27 and isolated as apeach solid (1.85 g, 85%): ¹H NMR (400 MHz, CDCl₃) δ 8.19 (s, 1H),7.71-7.62 (m, 1H), 7.35-7.28 (m, 1H), 7.26-7.21 (m, 2H), 4.25 (s, 2H),2.95-2.70 (m, 2H), 2.52-2.26 (m, 2H); ¹⁹F NMR (376 MHz, CDCl₃) δ−66.74;ESIMS m/z 266 ([M+H]⁺).

2-Chloro-N-(2-chloro-4,5-dimethylphenyl)acetamide (C38)

The title compound was prepared from commercial starting materials andisolated as a brown solid (2.77 g, 93%): mp 124-128° C.; ¹H NMR (400MHz, CDCl₃) δ 8.77 (s, 1H), 8.10 (s, 1H), 7.16 (s, 1H), 4.22 (s, 2H),2.25 (s, 3H), 2.22 (s, 3H); ¹³C NMR (101 MHz, CDCl₃) δ 163.66, 136.42,134.44, 131.01, 129.65, 122.41, 120.50, 43.13, 19.65, 19.21; EIMS m/z232.

2-Chloro-N-(2-(methoxymethyl)phenyl)acetamide (C39)

The title compound was prepared from compound C29 and isolated as anoff-white solid (1.423 g, 99%): ¹H NMR (400 MHz, CDCl₃) δ 9.87-9.67 (m,1H), 8.24-8.14 (m, 1H), 7.36 (td, J=7.8, 1.7 Hz, 1H), 7.21 (dd, J=7.6,1.7 Hz, 1H), 7.11 (td, J=7.5, 1.2 Hz, 1H), 4.53 (s, 2H), 4.21 (s, 2H),3.45 (s, 3H); ¹³C NMR (126 MHz, CDCl₃) δ 164.33, 136.89, 129.26, 129.23,126.86, 124.57, 121.66, 73.81, 58.14, 43.08; EIMS m/z 213.

N-(2-(sec-Butyl)-5-methoxyphenyl)-2-chloroacetamide (C40)

The title compound was prepared from compound C31 and isolated as abrown oil (2.0 g, used without purification): ¹H NMR (400 MHz, CDCl₃) δ8.36 (s, 1H), 7.46 (d, J=2.8 Hz, 1H), 7.15 (d, J=8.8 Hz, 1H), 6.77 (dd,J=3.2, 5.6 Hz, 1H), 4.26 (s, 2H), 3.79 (s, 3H), 2.72-2.65 (m, 1H),1.65-1.55 (m, 2H), 1.25 (dd, J=2.4, 6.8 Hz, 3H), 0.87 (t, J=7.2 Hz, 3H);ESIMS m/z 256 ([M+H]⁺).

2-Chloro-N-(5-chloro-2-(trifluoromethoxy)phenyl)acetamide (C41)

The title compound was prepared from commercially available startingmaterials and isolated as a light pink solid (4.3 g, 96%): mp 72-74° C.;¹H NMR (400 MHz, CDCl₃) δ 8.74 (s, 1H), 8.50 (d, J=2.5 Hz, 1H), 7.23(dq, J=8.8, 1.5 Hz, 1H), 7.15 (dd, J=8.8, 2.5 Hz, 1H), 4.23 (s, 2H); ¹⁹FNMR (376 MHz, CDCl₃) δ−58.01; ESIMS m/z 288 ([M+H]⁺).

2-Chloro-N-(5-chloro-2-(2,2,2-trifluoroethoxy)phenyl)acetamide (C42)

The title compound was prepared from compound C33 and isolated as a tansolid (3.45 g, 97%): mp 116-118° C.; ¹H NMR (400 MHz, CDCl₃) δ 8.97 (s,1H), 8.46 (d, J=2.6 Hz, 1H), 7.09 (dd, J=8.7, 2.5 Hz, 1H), 6.82 (d,J=8.8 Hz, 1H), 4.43 (q, J=7.8 Hz, 2H), 4.21 (s, 2H); ¹⁹F NMR (376 MHz,CDCl₃) δ−74.09; ESIMS m/z 302 ([M+H]⁺).

2-Imino-3-(5,6,7,8-tetrahydronaphthalen-1-yl)thiazolidin-4-one (C43)

The title compound was prepared from commercially available startingmaterials and isolated as a tan solid (1.91 g, 82%): mp 102-106° C.; ¹HNMR (400 MHz, CDCl₃) δ 9.19 (s, 1H), 7.25-7.07 (m, 2H), 6.92 (dd, J=7.3,1.7 Hz, 1H), 4.28-4.09 (m, 2H), 2.77 (d, J=5.5 Hz, 2H), 2.39 (q, J=5.5,3.9 Hz, 2H), 1.69 (d, J=7.0 Hz, 4H); ¹³C NMR (101 MHz, CDCl₃) δ 131.14,126.63, 125.92, 29.50, 24.21, 22.46, 22.36; ESIMS m/z 247 ([M+H]⁺).

Example 33: Preparation of 3-(2-butylphenyl)-2-iminothiazolidin-4-one(C44)

To a solution of N-(2-butylphenyl)-2-chloroacetamide (C34; 1.41 g, 6.3mmol) in acetone (6.3 mL) was added potassium thiocyanate (1.22 g, 12.5mmol) in portions. The reaction mixture was stirred at reflux for 5 hand at room temperature overnight. Cesium carbonate (0.102 g, 0.31 mmol)was added slowly, and the reaction mixture was stirred for 30 min. Thesolution was filtered through Celite® and the filtrate was concentrated.Purification by flash chromatography (0-60% ethyl acetate/hexanes)provided the title compound as a red oil (1.50 g, 96%): ¹H NMR (400 MHz,CDCl₃) δ 7.44-7.37 (m, 2H), 7.37-7.30 (m, 1H), 7.10 (dd, J=7.5, 1.2 Hz,1H), 4.08 (s, 2H), 2.50-2.31 (m, 2H), 1.58-1.48 (m, 2H), 1.38-1.28 (m,2H), 0.90 (t, J=7.3 Hz, 3H); ¹³C NMR (101 MHz, CDCl₃) δ 171.58, 161.18,141.58, 130.91, 130.59, 129.40, 127.94, 34.34, 32.41, 31.37, 31.18,23.03, 14.27; ESIMS m z 249 ([M+H]⁺).

The following compounds were prepared according to the procedure inExample 33.

3-(2-(2-Cyclopropylethyl)phenyl)-2-iminothiazolidin-4-one (C45)

The title compound was prepared from compound C35 and isolated as abrown solid (303 mg, 68%): ¹H NMR (400 MHz, CDCl₃) δ 7.90 (s, 1H), 7.67(d, J=7.9 Hz, 1H), 7.25-7.19 (m, 2H), 7.18 (dd, J=6.8, 2.0 Hz, 1H), 3.89(d, J=3.2 Hz, 2H), 2.72 (t, J=7.5 Hz, 2H), 1.51 (q, J=7.3 Hz, 2H), 0.70(tt, J=6.9, 3.0 Hz, 1H), 0.51-0.38 (m, 2H), 0.07 (dt, J=5.8, 2.9 Hz,2H); ¹³C NMR (101 MHz, CDCl₃) δ 163.67, 135.15, 134.34, 130.36, 127.27,127.08, 124.79, 111.46, 37.94, 35.73, 31.66, 11.09, 5.16; ESIMS m/z 261([M+H]⁺).

(E)-2-Imino-3-(2-(3,3,3-trifluoroprop-1-en-1-yl)phenyl)thiazolidin-4-one(C46)

The title compound was prepared from compound C36 and isolated as a redsolid (795 mg, 89%): ¹H NMR (400 MHz, CDCl₃) δ 7.94 (s, 1H), 7.69 (d,J=7.2 Hz, 1H), 7.60-7.42 (m, 2H), 7.26-7.22 (m, 1H), 6.96 (d, J=16.0 Hz,1H), 6.28-6.11 (m, 1H), 4.12 (d, J=7.2 Hz, 2H); ¹⁹F NMR (376 MHz, CDCl₃)δ−63.82; ESIMS m/z 287 ([M+H]⁺).

2-Imino-3-(2-(3,3,3-trifluoropropyl)phenyl)thiazolidin-4-one (C47)

The title compound was prepared from intermediate C37 and isolated as ared solid (1.85 g, 88%): ¹H NMR (400 MHz, CDCl₃) δ 7.90 (s, 1H),7.57-7.31 (m, 3H), 7.16 (dd, J=7.7, 1.6 Hz, 1H), 4.10 (d, J=1.8 Hz, 2H),2.76-2.60 (m, 2H), 2.43-2.22 (m, 2H); ¹⁹F NMR (376 MHz, CDCl₃) δ−67.08;¹³C NMR (101 MHz, CDCl₃) δ 161.07, 137.88, 130.88, 130.67, 129.84,128.99, 128.33, 125.58, 34.91, 34.63, 24.19; ESIMS m/z 289 ([M+H]⁺).

3-(2-Chloro-4,5-dimethylphenyl)-2-iminothiazolidin-4-one (C48)

The title compound was prepared from compound C38 and isolated as abrown oil (2.62 g, 82%): ¹H NMR (400 MHz, DMSO-d₆) δ 9.28 (s, 1H), 7.39(s, 1H), 7.15-7.12 (m, 1H), 4.25-4.14 (m, 2H), 2.25 (s, 3H), 2.22 (s,3H); ¹³C NMR (101 MHz, DMSO-d₆) δ 170.99, 156.80, 139.50, 136.47,131.52, 130.07, 130.01, 128.53, 33.63, 18.82, 18.62; ESIMS m/z 255([M+H]⁺).

2-Imino-3-(2-(methoxymethyl)phenyl)thiazolidin-4-one (C49)

The title compound was prepared from compound C39 and isolated as abrown oil (1.88 g, 72%): ¹H NMR (400 MHz, DMSO-d₆) δ 9.23 (s, 1H),7.51-7.36 (m, 3H), 7.18 (dd, J=7.5, 1.5 Hz, 1H), 4.34-3.95 (m, 4H), 3.22(s, 3H); ¹³C NMR (101 MHz, CDCl₃) δ 170.87, 160.31, 136.49, 129.91,129.71, 129.24, 129.12, 71.07, 58.34, 33.98; ESIMS m/z 237 ([M+H]⁺).

3-(2-(sec-Butyl)-5-methoxyphenyl)-2-iminothiazolidin-4-one (C50)

The title compound was prepared from compound C40 and isolated as anoff-white solid (0.5 g, 15%): mp 115-117° C.; ¹H NMR (400 MHz, DMSO-d₆)δ 9.20 (d, J=5.2 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 6.99 (dd, J=2.8, 8.8Hz, 1H), 6.68 (d, J=2.0 Hz, 1H), 4.29-4.09 (m, 2H), 3.73 (s, 3H),2.38-2.31 (m, 1H), 1.58-1.39 (m, 2H), 1.05 (dd, J=6.8, 10.8 Hz, 3H),0.75-0.63 (m, 3H); ESIMS m/z 279 ([M+H]⁺).

3-(5-Chloro-2-(trifluoromethoxy)phenyl)-2-iminothiazolidin-4-one (C51)

The title compound was prepared from compound C41 and isolated as alight pink solid (2.49 g, 52%): mp 109-111° C.; ¹H NMR (400 MHz, CDCl₃)δ 7.94 (s, 1H), 7.51-7.45 (m, 1H), 7.36 (q, J=3.4 Hz, 2H), 4.19-4.02 (m,2H); ¹⁹F NMR (376 MHz, CDCl₃) δ −57.42; ESIMS m/z 311 ([M+H]⁺).

3-(5-Chloro-2-(2,2,2-trifluoroethoxy)phenyl)-2-iminothiazolidin-4-one(C52)

The title compound was prepared from compound C42 and isolated as ayellow solid (3.12 g, 92%): mp 114-116° C.; ¹H NMR (400 MHz, CDCl₃) δ7.84 (s, 1H), 7.43 (dd, J=9.0, 2.5 Hz, 1H), 7.29 (d, J=2.6 Hz, 1H), 7.00(d, J=8.9 Hz, 1H), 4.39-4.30 (m, 2H), 4.07 (d, J=6.0 Hz, 2H); ¹⁹F NMR(376 MHz, CDCl₃) δ−74.16; ESIMS m/z 325 ([M+H]⁺).

2-Imino-3-(5,6,7,8-tetrahydronaphthalen-1-yl)thiazolidin-4-one (C53)

The title compound was prepared from compound C43 and isolated as a tansolid (1.91 g, 82%): mp 102-106° C.; ¹H NMR (400 MHz, CDCl₃) δ 9.19 (s,1H), 7.25-7.07 (m, 2H), 6.92 (dd, J=7.3, 1.7 Hz, 1H), 4.28-4.09 (m, 2H),2.77 (d, J=5.5 Hz, 2H), 2.39 (q, J=5.5, 3.9 Hz, 2H), 1.69 (d, J=7.0 Hz,4H); ¹³C NMR (101 MHz, CDCl₃) δ 131.14, 126.63, 125.92, 29.50, 24.21,22.46, 22.36; ESIMS m/z 247 ([M+H]⁺).

TABLE 2 Analytical Data for Compounds in Table 1 Melting Cmpd. Point No.(° C.) MASS SPEC NMR A1 ESIMS m/z 624 ¹H NMR (400 MHz, CDCl₃) δ 8.55 (s,1H), ([M + H]⁺) 8.12-8.05 (m, 2H), 7.83-7.78 (m, 2H), 7.39 (dd, J = 8.8,1.2 Hz, 2H), 7.31 (dd, J = 17.6, 8.1 Hz, 4H), 6.86 (s, 1H), 4.46-4.30(m, 2H), 3.99 (d, J = 1.0 Hz, 2H), 3.02 (t, J = 7.3 Hz, 2H), 2.58 (p, J= 6.8 Hz, 1H), 2.34 (t, J = 0.7 Hz, 3H), 1.17 (dd, J = 13.5, 6.9 Hz,6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03 A2  154-155.5 ESIMS m/z 610 ¹HNMR (400 MHz, CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.12-8.06 (m, 2H),7.84-7.77 (m, 2H), 7.49-7.43 (m, 2H), 7.39 (dq, J = 8.9, 0.9 Hz, 2H),7.34-7.27 (m, 3H), 7.06 (dt, J = 7.8, 1.0 Hz, 1H), 4.37 (ddt, J = 28.4,10.8, 7.3 Hz, 2H), 4.00 (d, J = 1.0 Hz, 2H), 3.01 (t, J = 7.3 Hz, 2H),2.68-2.60 (m, 1H), 1.19 (dd, J = 10.0, 6.9 Hz, 6H); ¹⁹F NMR (376 MHz,CDCl₃) δ −58.03 A3 ESIMS m/z 596 ¹H NMR (400 MHz, CDCl₃) δ 8.55 (s, 1H),([M + H]⁺) 8.22-8.13 (m, 2H), 7.84-7.74 (m, 2H), 7.43-7.33 (m, 3H),7.29-7.22 (m, 3H), 6.95-6.87 (m, 1H), 4.04 (t, J = 1.2 Hz, 2H), 2.64 (p,J = 6.9 Hz, 1H), 2.36 (s, 3H), 1.22 (dd, J = 26.5, 6.8 Hz, 6H); ¹⁹F NMR(376 MHz, CDCl₃) δ −58.03 A4 ESIMS m/z 660 ¹H NMR (400 MHz, CDCl₃) δ8.59 (s, 1H), ([M + H]⁺) 8.22 (d, J = 8.1 Hz, 2H), 7.85-7.76 (m, 2H),7.58 (d, J = 8.2 Hz, 2H), 7.41 (dd, J = 9.0, 1.0 Hz, 2H), 7.33 (d, J =8.1 Hz, 1H), 7.28 (d, J = 1.9 Hz, 1H), 6.89-6.82 (m, 1H), 4.68 (q, J =12.9 Hz, 1H), 4.55-4.44 (m, 1H), 3.98 (d, J = 0.6 Hz, 2H), 2.55 (p, J =6.9 Hz, 1H), 2.34 (d, J = 0.7 Hz, 3H), 1.15 (dd, J = 11.2, 6.9 Hz, 6H);¹⁹F NMR (376 MHz, CDCl₃) δ −58.02, −104.24, −104.31 A5 ESIMS m/z 612 ¹HNMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺) 8.04-7.97 (m, 2H),7.85-7.76 (m, 2H), 7.43-7.33 (m, 3H), 7.10 (dd, J = 7.8, 1.7 Hz, 1H),7.05-6.89 (m, 4H), 4.43 (t, J = 6.4 Hz, 2H), 4.00-3.74 (m, 4H), 2.88 (t,J = 6.3 Hz, 2H), 1.20 (t, J = 7.0 Hz, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ−58.02 A6 183-185 ESIMS m/z 624 ¹H NMR (500 MHz, CDCl₃) δ 8.55 (d, J =1.3 ([M + H]⁺) Hz, 1H), 8.10 (d, J = 7.7 Hz, 2H), 7.84-7.74 (m, 2H),7.46-7.35 (m, 4H), 7.35-7.27 (m, 3H), 7.09 (d, J = 7.9 Hz, 1H), 4.38 (q,J = 7.0 Hz, 2H), 3.99 (s, 2H), 3.02 (t, J = 7.5 Hz, 2H), 2.41 (t, J =8.0 Hz, 2H), 1.31 (q, J = 7.4 Hz, 4H), 0.87 (t, J = 7.3 Hz, 3H); ¹⁹F NMR(471 MHz, CDCl₃) δ −58.03 A7 172-175 ESIMS m/z 636 ¹H NMR (500 MHz,CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.10 (d, J = 7.8 Hz, 2H), 7.82-7.75(m, 2H), 7.48-7.27 (m, 7H), 7.09 (d, J = 7.7 Hz, 1H), 4.38 (q, J = 7.6Hz, 2H), 4.00 (d, J = 2.0 Hz, 2H), 3.02 (t, J = 7.5 Hz, 2H), 2.52 (t, J= 7.9 Hz, 2H), 1.45 (q, J = 7.5 Hz, 2H), 0.74-0.60 (m, 1H), 0.39 (d, J =7.8 Hz, 2H), −0.03 (d, J = 4.9 Hz, 2H); ¹⁹F NMR (471 MHz, CDCl₃) δ−58.03 A8 177-183 ESIMS m/z 664 ¹H NMR (500 MHz, CDCl₃) δ 8.55 (d, J =1.4 ([M + H]⁺) Hz, 1H), 8.14-8.06 (m, 2H), 7.85-7.74 (m, 2H), 7.46 (t, J= 7.6 Hz, 1H), 7.43-7.34 (m, 4H), 7.30 (d, J = 7.9 Hz, 2H), 7.14 (d, J =7.8 Hz, 1H), 4.39 (dtd, J = 18.3, 10.9, 7.6 Hz, 2H), 4.01 (d, J = 1.6Hz, 2H), 3.03 (t, J = 7.5 Hz, 2H), 2.66 (t, J = 8.5 Hz, 2H), 2.46-2.31(m, 2H); ¹⁹F NMR (471 MHz, CDCl₃) δ −58.03, −67.06 A9 218-221 ESIMS m/z662 ¹H NMR (500 MHz, CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.14-8.06 (m,2H), 7.85-7.76 (m, 2H), 7.71-7.60 (m, 1H), 7.53 (td, J = 9.3, 7.8, 4.8Hz, 2H), 7.39 (d, J = 8.5 Hz, 2H), 7.30 (d, J = 7.9 Hz, 2H), 7.22 (d, J= 7.4 Hz, 1H), 6.91 (d, J = 16.0 Hz, 1H), 6.25-6.15 (m, 1H), 4.45- 4.31(m, 2H), 4.07-3.97 (m, 2H), 3.03 (t, J = 7.5 Hz, 2H); ¹⁹F NMR (471 MHz,CDCl₃) δ −58.03, −63.83 A10  116-120, ESIMS m/z 612 ¹H NMR (400 MHz,CDCl₃) δ 8.55 (s, 1H), 148-151 ([M + H]⁺) 8.13-8.05 (m, 2H), 7.83-7.72(m, 2H), 7.42-7.34 (m, 2H), 7.30 (d, J = 8.2 Hz, 2H), 7.04-6.98 (m, 1H),6.85 (s, 2H), 4.39 (t, J = 7.5 Hz, 2H), 3.97 (d, J = 0.8 Hz, 2H), 3.81(s, 3H), 3.04 (t, J = 7.5 Hz, 2H), 2.12 (s, 3H); ¹⁹F NMR (376 MHz,CDCl₃) δ −58.03 A11  199-200.5 ESIMS m/z 600 ¹H NMR (500 MHz, CDCl₃) δ8.55 (d, J = 1.4 ([M + H]⁺) Hz, 1H), 8.11 (dd, J = 8.1, 1.5 Hz, 2H),7.80 (dd, J = 8.8, 1.6 Hz, 2H), 7.39 (d, J = 8.5 Hz, 2H), 7.31 (d, J =7.8 Hz, 2H), 7.23 (d, J = 5.6 Hz, 1H), 7.12 (t, J = 9.0 Hz, 1H), 7.05(d, J = 6.8 Hz, 1H), 4.40 (t, J = 7.5 Hz, 2H), 4.08- 3.91 (m, 2H), 3.05(t, J = 7.5 Hz, 2H), 2.36 (s, 3H); ¹⁹F NMR (471 MHz, CDCl₃) δ −58.03,−124.88 A12 222-228 ESIMS m/z 617 ¹H NMR (500 MHz, CDCl₃) δ 8.55 (d, J =1.4 ([M + H]⁺) Hz, 1H), 8.14-8.05 (m, 2H), 7.83-7.75 (m, 2H), 7.40 (dd,J = 16.9, 8.4 Hz, 3H), 7.30 (d, J = 7.9 Hz, 2H), 7.23 (d, J = 8.3 Hz,1H), 7.08 (s, 1H), 4.40 (t, J = 7.5 Hz, 2H), 4.00 (q, J = 18.1 Hz, 2H),3.05 (t, J = 7.5 Hz, 2H), 2.37 (s, 3H); ¹⁹F NMR (471 MHz, CDCl₃) δ−58.03 A13  98-105 ESIMS m/z 612 ¹H NMR (500 MHz, CDCl₃) δ 8.55 (d, J =1.2 ([M + H]⁺) Hz, 1H), 8.15-8.05 (m, 2H), 7.84-7.77 (m, 2H), 7.39 (d, J= 8.5 Hz, 2H), 7.30 (d, J = 7.8 Hz, 2H), 7.21 (d, J = 8.5 Hz, 1H), 6.96(s, 1H), 6.92 (d, J = 8.4 Hz, 1H), 4.38 (t, J = 7.5 Hz, 2H), 4.03-3.89(m, 2H), 3.76 (d, J = 1.3 Hz, 3H), 3.04 (t, J = 7.6 Hz, 2H), 2.31 (s,3H); ¹⁹F NMR (471 MHz, CDCl₃) δ −58.03 A14 243-249 ESIMS m/z 650 ¹H NMR(500 MHz, CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.10 (d, J = 7.8 Hz, 2H),7.82-7.77 (m, 2H), 7.69 (d, J = 8.1 Hz, 1H), 7.40 (t, J = 8.9 Hz, 3H),7.29 (d, J = 7.8 Hz, 2H), 7.10 (s, 1H), 4.39 (q, J = 7.2, 6.7 Hz, 2H),4.06-3.90 (m, 2H), 3.04 (t, J = 7.5 Hz, 2H), 2.46 (s, 3H); ¹⁹F NMR (471MHz, CDCl₃) δ −58.03, −61.12 A15 193-199 ESIMS m/z 624 ¹H NMR (500 MHz,CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.10 (d, J = 7.8 Hz, 2H), 7.79 (d, J =8.5 Hz, 2H), 7.39 (d, J = 8.5 Hz, 2H), 7.29 (d, J = 7.9 Hz, 2H),7.25-7.16 (m, 2H), 6.89 (s, 1H), 4.38 (q, J = 7.9 Hz, 2H), 3.98 (d, J =2.6 Hz, 2H), 3.03 (t, J = 7.5 Hz, 2H), 2.35-2.32 (m, 5H), 1.61-1.55 (m,2H), 0.90 (t, J = 7.4 Hz, 3H); ¹⁹F NMR (471 MHz, CDCl₃) δ −58.03 A16195-197 ESIMS m/z 626 ¹H NMR (500 MHz, CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺)8.09 (d, J = 7.8 Hz, 2H), 7.84-7.75 (m, 2H), 7.38 (d, J = 8.5 Hz, 2H),7.30 (d, J = 7.9 Hz, 2H), 7.18 (d, J = 8.5 Hz, 1H), 6.97 (s, 1H), 6.90(d, J = 8.4 Hz, 1H), 4.39 (td, J = 7.7, 3.3 Hz, 2H), 4.01 (qd, J = 7.8,7.3, 3.0 Hz, 2H), 3.95 (d, J = 7.7 Hz, 2H), 3.04 (t, J = 7.5 Hz, 2H),2.31 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H); ¹⁹F NMR (471 MHz, CDCl₃) δ−58.03 A17 ESIMS m/z 642 ¹H NMR (400 MHz, CDCl₃) δ 8.56 (s, 1H), ([M +H]⁺) 8.09 (d, J = 8.2 Hz, 2H), 7.82-7.76 (m, 2H), 7.39 (d, J = 8.4 Hz,2H), 7.29 (d, J = 8.2 Hz, 2H), 7.06 (d, J = 10.7 Hz, 1H), 6.89 (d, J =7.1 Hz, 1H), 4.39 (ddt, J = 30.3, 10.8, 7.3 Hz, 2H), 3.98 (d, J = 1.1Hz, 2H), 3.03 (t, J = 7.3 Hz, 2H), 2.63-2.46 (m, 1H), 2.27-2.19 (m, 3H),1.21-1.11 (m, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03, −114.48 A18194-198 ESIMS m/z 631 ¹H NMR (500 MHz, CDCl₃) δ 8.54 (s, 1H), ([M + H]⁺)8.14-8.07 (m, 2H), 7.83-7.75 (m, 2H), 7.39 (d, J = 8.5 Hz, 2H),7.33-7.28 (m, 3H), 7.02 (s, 1H), 4.40 (t, J = 7.6 Hz, 2H), 3.99 (q, J =18.1 Hz, 2H), 3.04 (t, J = 7.6 Hz, 2H), 2.26 (s, 3H), 2.25 (s, 3H); ¹⁹FNMR (471 MHz, CDCl₃) δ −58.03 A19 206-210 ESIMS m/z 638 ¹H NMR (300 MHz,CDCl₃) δ 8.56 (d, J = 0.5 ([M + H]⁺) Hz, 1H), 8.07 (t, J = 8.5 Hz, 2H),7.83-7.76 (m, 2H), 7.39 (d, J = 8.5 Hz, 2H), 7.33-7.24 (m, 4H), 6.87 (d,J = 9.5 Hz, 1H), 5.17-5.00 (m, 1H), 4.00-3.89 (m, 2H), 3.06 (ddd, J =29.0, 13.6, 6.7 Hz, 1H), 2.86-2.70 (m, 1H), 2.64-2.50 (m, 1H), 2.35 (d,J = 6.8 Hz, 3H), 1.30-1.11 (m, 9H); ¹³C NMR (126 MHz, CDCl₃) δ 172.57,163.43, 143.01, 142.91, 141.46, 139.37, 139.29, 136.88, 135.58, 131.89,131.41, 131.37, 129.80, 129.75, 128.63, 128.58, 128.25, 126.84, 126.61,126.56, 122.40, 121.18, 121.16, 74.25, 42.06, 33.01, 28.44, 23.84,23.56, 23.52, 20.84; ¹⁹F NMR (471 MHz, CDCl₃) δ −58.03 A20 HRMS-ESI(m/z) ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), [M + H]⁺ calcd for 8.20(d, J = 8.0 Hz, 2H), 7.86-7.74 (m, 2H), C₃₁H₂₈F₄N₅O₄S, 7.50-7.37 (m,4H), 7.37-7.27 (m, 2H), 641.172; found, 6.90-6.82 (m, 1H), 5.86-5.67 (m,1H), 642.1805 4.61-4.29 (m, 2H), 4.06-3.93 (m, 2H), 2.59 (m, 1H), 2.34(d, J = 1.8 Hz, 3H), 1.18 (m, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.02,−185.29 A21 HRMS-ESI (m/z) ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), [M +H]⁺ calcd for 8.21 (d, J = 8.1 Hz, 2H), 7.86-7.76 (m, 2H),C₃₀H₂₃F₇N₅O₅S, 7.52-7.35 (m, 3H), 7.06 (d, J = 2.0 Hz, 1H), 697.123;found, 6.95 (dd, J = 8.5, 1.4 Hz, 1H), 5.89-5.64 (m, 698.1315 1H),4.55-4.39 (m, 2H), 4.34 (qd, J = 8.1, 6.3 Hz, 2H), 4.13-4.04 (m, 1H),4.04-3.90 (m, 2H), 2.42-2.29 (m, 4H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03,−74.30, −185.34 A22 HRMS-ESI (m/z) ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s,1H), [M + H]⁺ calcd for 8.22 (d, J = 8.1 Hz, 2H), 7.88-7.74 (m, 2H),C₂₉H₂₀ClF₇N₅O₅S, 7.52-7.37 (m, 4H), 7.28 (d, J = 2.5 Hz, 1H), 717.0684;found, 7.00 (dd, J = 8.9, 1.0 Hz, 1H), 5.76 (ddd, J = 718.0757 48.7,7.9, 4.4 Hz, 1H), 4.59-4.43 (m, 2H), 4.43-4.26 (m, 3H), 4.07-3.89 (m,2H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.02, −74.18, −185.30 A23 HRMS-ESI(m/z) ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), [M + H]⁺ calcd for 8.21(d, J = 8.0 Hz, 2H), 7.87-7.76 (m, 2H), C₃₀H₂₅ClF₄N₅O₄S, 7.50-7.35 (m,5H), 7.09 (d, J = 2.1 Hz, 1H), 661.1174; found, 5.86-5.65 (m, 1H),4.63-4.29 (m, 3H), 662.1251 4.02 (t, J = 0.9 Hz, 2H), 2.61 (dtd, J =9.6, 6.9, 3.5 Hz, 1H), 1.18 (ddd, J = 13.9, 6.9, 2.2 Hz, 6H); ¹⁹F NMR(376 MHz, CDCl₃) δ −58.02, −185.31 A24 ESIMS m/z 678 ¹H NMR (400 MHz,CDCl₃) δ 8.58 (s, 1H), ([M + H]⁺) 8.20 (d, J = 8.0 Hz, 2H), 7.84-7.78(m, 2H), 7.48-7.38 (m, 6H), 7.32 (ddt, J = 5.8, 4.7, 3.1 Hz, 1H), 7.07(dd, J = 7.7, 1.0 Hz, 1H), 5.74 (ddd, J = 48.6, 8.1, 2.9 Hz, 1H), 4.58-4.25 (m, 2H), 4.02 (t, J = 1.1 Hz, 2H), 2.70- 2.58 (m, 1H), 1.25-1.17(m, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −85.89, −87.85, −185.35, −185.61 A25ESIMS m/z 712 ¹H NMR (400 MHz, CDCl₃) δ 8.58 (s, 1H), ([M]⁺) 8.21 (d, J= 8.0 Hz, 2H), 7.85-7.77 (m, 2H), 7.48-7.36 (m, 6H), 7.09 (d, J = 2.2Hz, 1H), 5.89-5.64 (m, 1H), 4.62-4.29 (m, 2H), 4.02 (d, J = 1.0 Hz, 2H),2.68-2.53 (m, 1H), 1.18 (ddd, J = 13.9, 6.8, 2.2 Hz, 6H); ¹⁹F NMR (376MHz, CDCl₃) δ −85.89, −87.85, −185.32, −185.54 A26 ESIMS m/z 692 ¹H NMR(400 MHz, CDCl₃) δ 8.58 (s, 1H), ([M + H]⁺) 8.21 (d, J = 7.9 Hz, 2H),7.81 (d, J = 9.0 Hz, 2H), 7.43 (dd, J = 17.5, 8.5 Hz, 4H), 7.34 (d, J =8.0 Hz, 1H), 7.28-7.26 (m, 1H), 6.87 (s, 1H), 5.82-5.67 (m, 1H), 4.47(m, 2H), 4.01 (s, 2H), 2.60 (m, 1H), 2.35 (s, 3H), 1.18 (ddd, J = 15.0,6.8, 2.2 Hz, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −85.89, −87.84 A27 ESIMSm/z 612 ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺) 8.01 (d, J =8.3 Hz, 2H), 7.81 (dd, J = 9.3, 2.6 Hz, 2H), 7.47-7.37 (m, 5H), 7.08 (d,J = 7.6 Hz, 1H), 6.96 (d, J = 8.2 Hz, 2H), 4.50-4.31 (m, 2H), 4.30-4.09(m, 2H), 3.86 (d, J = 1.0 Hz, 2H), 3.19 (s, 3H), 2.86 (t, J = 6.5 Hz,2H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03 A28 ESIMS m/z 654 ¹H NMR (400MHz, CDCl₃) δ 8.55 (d, J = 0.7 ([M + H]⁺) Hz, 1H), 8.09 (d, J = 8.1 Hz,2H), 7.80 (d, J = 8.9 Hz, 2H), 7.39 (d, J = 8.6 Hz, 2H), 7.31- 7.27 (m,3H), 7.01 (dd, J = 8.7, 2.7 Hz, 1H), 6.58 (dd, J = 4.5, 2.7 Hz, 1H),4.49-4.28 (m, 2H), 4.01-3.95 (m, 2H), 3.78 (s, 3H), 3.02 (td, J = 7.3,2.9 Hz, 2H), 2.25 (p, J = 7.1 Hz, 1H), 1.54 (m, 2H), 1.13 (dd, J = 17.1,6.8 Hz, 3H), 0.72 (dt, J = 9.0, 7.4 Hz, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ−58.03 A29 221-223 ESIMS m/z 686 ¹H NMR (400 MHz, CDCl₃) δ 8.55 (s, 1H),([M + H]⁺) 8.11 (d, J = 8.2 Hz, 2H), 7.82-7.77 (m, 2H), 7.50 (dd, J =8.9, 2.5 Hz, 1H), 7.39 (dd, J = 8.7, 1.2 Hz, 3H), 7.36-7.28 (m, 3H),4.41 (t, J = 7.4 Hz, 2H), 4.07-3.89 (m, 2H), 3.05 (t, J = 7.4 Hz, 2H);¹⁹F NMR (376 MHz, CDCl₃) δ −57.30, −58.03 A30 195-197 ESIMS m/z 700 ¹HNMR (400 MHz, CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.14-8.03 (m, 2H),7.84-7.73 (m, 2H), 7.48-7.35 (m, 4H), 7.35-7.28 (m, 2H), 6.98 (d, J =8.9 Hz, 1H), 4.41 (td, J = 7.2, 2.9 Hz, 2H), 4.36-4.29 (m, 2H), 3.97 (d,J = 3.8 Hz, 2H), 3.05 (t, J = 7.4 Hz, 2H); ¹⁹F NMR (376 MHz, CDCl₃) δ−58.03, −74.15 A31 ESIMS m/z 680 ¹H NMR (400 MHz, CDCl₃) δ 8.55 (s, 1H),([M + H]⁺) 8.13-8.02 (m, 2H), 7.84-7.75 (m, 2H), 7.42-7.35 (m, 2H), 7.30(d, J = 8.2 Hz, 2H), 7.24-7.19 (m, 1H), 7.06-7.01 (m, 1H), 6.94 (d, J =8.5 Hz, 1H), 4.35 (dq, J = 33.5, 7.7 Hz, 4H), 4.03-3.85 (m, 2H), 3.04(t, J = 7.5 Hz, 2H), 2.34 (s, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03,−74.26 A32 ESIMS m/z 610 ¹H NMR (400 MHz, CDCl₃) δ 8.55 (s, 1H), ([M +H]⁺) 8.12-8.07 (m, 2H), 7.82-7.75 (m, 2H), 7.41-7.36 (m, 2H), 7.30 (m,3H), 7.23- 7.13 (m, 2H), 4.40-4.32 (m, 2H), 4.00 (s, 2H), 3.02 (t, J =7.5 Hz, 2H), 2.42 (q, J = 7.5 Hz, 2H), 2.12 (s, 3H), 1.17 (t, J = 7.6Hz, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03 A33 203-210 ESIMS m/z 622 ¹HNMR (400 MHz, CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.13-8.06 (m, 2H),7.84-7.76 (m, 2H), 7.39 (d, J = 8.6 Hz, 2H), 7.30 (d, J = 8.2 Hz, 2H),7.25-7.14 (m, 2H), 6.97-6.85 (m, 1H), 4.38 (t, J = 7.5 Hz, 2H),4.00-3.93 (m, 2H), 3.04 (t, J = 7.5 Hz, 2H), 2.82 (s, 2H), 2.50-2.36 (m,2H), 1.81-1.72 (m, 4H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03 A34 ESIMS m/z628 ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺) 8.20 (d, J = 8.1Hz, 2H), 7.82-7.78 (m, 2H), 7.49-7.38 (m, 7H), 7.07 (d, J = 7.9 Hz, 1H),5.73 (dd, J = 48.3, 8.5 Hz, 1H), 4.62-4.24 (m, 2H), 4.02 (t, J = 1.1 Hz,2H), 2.65 (td, J = 6.9, 2.9 Hz, 1H), 1.27-1.15 (m, 6H); ¹⁹F NMR (376MHz, CDC1₃) δ −58.03, −185.35, −185.60 A35 132-136 ESIMS m/z 654 ¹H NMR(400 MHz, CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.11-8.06 (m, 2H), 7.82-7.76(m, 2H), 7.39 (d, J = 8.6 Hz, 2H), 7.30 (d, J = 8.1 Hz, 2H), 7.20-7.15(m, 1H), 6.97 (d, J = 2.2 Hz, 1H), 6.89 (d, J = 8.3 Hz, 1H), 4.45-4.25(m, 3H), 3.94 (d, J = 2.2 Hz, 2H), 3.07-2.99 (m, 2H), 2.30 (s, 3H),1.67-1.55 (m, 2H), 1.18 (dd, J = 25.1, 6.1 Hz, 3H), 0.86 (dt, J = 11.1,7.4 Hz, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03 A36 ESIMS m/z 704 ¹H NMR(400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺) 8.22 (d, J = 8.0 Hz, 2H),7.84-7.76 (m, 2H), 7.51 (dd, J = 8.9, 2.6 Hz, 1H), 7.47 (d, J = 8.2 Hz,2H), 7.42-7.37 (m, 3H), 7.37-7.34 (m, 1H), 5.78 (ddd, J = 48.7, 8.3, 2.7Hz, 1H), 4.62-4.31 (m, 2H), 4.09-3.92 (m, 2H); ¹⁹F NMR (376 MHz, CDCl₃)δ −57.31, −58.03, −185.16, −185.28 A37 ESIMS m/z 630 ¹H NMR (400 MHz,CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺) 8.21 (d, J = 8.1 Hz, 2H), 7.80 (d, J =9.1 Hz, 2H), 7.46 (d, J = 8.1 Hz, 2H), 7.40 (d, J = 8.6 Hz, 2H), 7.04(d, J = 8.1 Hz, 1H), 6.86 (s, 2H), 5.77 (dd, J = 48.2, 8.9 Hz, 1H),4.58- 4.30 (m, 2H), 4.00 (s, 2H), 3.83 (s, 3H), 2.14 (s, 3H); ¹⁹F NMR(376 MHz, CDCl₃) δ −58.02, −185.15, −185.24 A38 167-172 ESIMS m/z 648 ¹HNMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺) 8.21 (d, J = 8.0 Hz,2H), 7.82-7.77 (m, 2H), 7.47 (d, J = 8.0 Hz, 2H), 7.40 (d, J = 8.6 Hz,2H), 7.32 (s, 1H), 7.04 (s, 1H), 5.88-5.68 (m, 1H), 4.60-4.30 (m, 2H),4.08-3.92 (m, 2H), 2.28 (s, 3H), 2.27 (s, 3H); ¹⁹F NMR (376 MHz, CDCl₃)δ −58.02, −185.09, −185.20 A39 ESIMS m/z 640 ¹H NMR (400 MHz, CDCl₃) δ8.57 (s, 1H), ([M + H]⁺) 8.21 (d, J = 8.1 Hz, 2H), 7.83-7.78 (m, 2H),7.46 (d, J = 7.9 Hz, 2H), 7.43-7.37 (m, 2H), 7.25-7.17 (m, 2H), 6.94 (d,J = 7.2 Hz, 1H), 5.77 (dd, J = 48.7, 8.4 Hz, 1H), 4.56-4.29 (m, 2H),4.07-3.79 (m, 2H), 2.83 (s, 2H), 2.63-2.36 (m, 2H), 1.79 (s, 4H); ¹⁹FNMR (376 MHz, CDCl₃) δ −58.03, −185.15, −185.19 A40 ESIMS m/z 630 ¹H NMR(400 MHz, CDCl₃) δ 8.58 (s, 1H), ([M + H]⁺) 8.13 (d, J = 8.1 Hz, 2H),7.83-7.77 (m, 2H), 7.40 (d, J = 8.3 Hz, 3H), 7.25-7.19 (m, 2H), 7.14(dd, J = 23.5, 7.7 Hz, 1H), 7.06-6.88 (m, 2H), 5.60 (d, J = 47.5 Hz,1H), 4.51 (dt, J = 21.5, 11.7 Hz, 2H), 4.43-3.88 (m, 4H), 1.27 (dt, J =29.3, 7.0 Hz, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.02, −186.52, −186.79A41 ESIMS m/z 672 ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺)8.21 (d, J = 8.0 Hz, 2H), 7.83-7.75 (m, 2H), 7.48-7.42 (m, 2H), 7.39(dq, J = 7.9, 1.1 Hz, 2H), 7.22-7.12 (m, 1H), 6.98 (d, J = 2.2 Hz, 1H),6.94-6.86 (m, 1H), 5.86-5.61 (m, 1H), 4.58-4.22 (m, 3H), 3.96 (d, J =2.1 Hz, 2H), 2.34-2.24 (m, 3H), 1.72-1.48 (m, 2H), 1.29-1.10 (m, 3H),0.96-0.81 (m, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.02, −185.33, −185.50A42 213-215 ESIMS m/z 628 ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M +H]⁺) 8.21 (d, J = 8.0 Hz, 2H), 7.83-7.77 (m, 2H), 7.44 (d, J = 8.2 Hz,2H), 7.40 (d, J = 8.5 Hz, 2H), 7.34 (t, J = 7.6 Hz, 1H), 7.24-7.16 (m,2H), 5.75 (dd, J = 47.2, 7.3 Hz, 1H), 4.61- 4.28 (m, 2H), 4.02 (s, 2H),3.51 (s, 3H), 2.42 (t, J = 7.6 Hz, 2H), 2.13 (s, 3H), 1.18 (td, J = 7.6,2.0 Hz, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03, −185.25, −185.28 A43ESIMS m/z 695 ¹H NMR (400 MHz, CDCl₃) δ 8.56 (s, 1H), ([M + H]⁺) 8.10(d, J = 8.2 Hz, 2H), 7.81 (d, J = 9.0 Hz, 2H), 7.43-7.36 (m, 4H), 7.30(d, J = 8.2 Hz, 2H), 7.08 (d, J = 2.1 Hz, 1H), 4.48-4.30 (m, 2H), 3.99(s, 2H), 3.03 (t, J = 7.2 Hz, 2H), 2.67-2.52 (m, 1H), 1.17 (dd, J =11.2, 6.8 Hz, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −85.89, −87.84 A44 ESIMSm/z 674 ¹H NMR (400 MHz, CDCl₃) δ 8.56 (s, 1H), ([M + H]⁺) 8.09 (d, J =8.2 Hz, 2H), 7.83-7.75 (m, 2H), 7.40 (d, J = 8.8 Hz, 2H), 7.35-7.27 (m,4H), 6.86 (s, 1H), 4.48-4.27 (m, 2H), 3.99 (d, J = 1.0 Hz, 2H), 3.02 (t,J = 7.3 Hz, 2H), 2.58 (p, J = 6.8 Hz, 1H), 2.34 (s, 3H), 1.17 (dd, J =13.5, 6.9 Hz, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −85.89, −87.84 A45 ESIMSm/z 660 ¹H NMR (400 MHz, CDCl₃) δ 8.56 (s, 1H), ([M + H]⁺) 8.11-8.06 (m,2H), 7.83-7.78 (m, 2H), 7.46 (dd, J = 4.1, 1.1 Hz, 2H), 7.39 (d, J = 8.9Hz, 2H), 7.34-7.27 (m, 3H), 7.06 (d, J = 7.8 Hz, 1H), 4.47-4.27 (m, 2H),4.00 (d, J = 1.0 Hz, 2H), 3.01 (t, J = 7.3 Hz, 2H), 2.64 (p, J = 6.8 Hz,1H), 1.19 (dd, J = 10.0, 6.9 Hz, 6H; ¹⁹F NMR (376 MHz, CDCl₃) δ −85.89,−87.84 A46 ESIMS m/z 659 ¹H NMR (400 MHz, CDCl₃) δ 8.56 (d, J = 1.5([M + H]⁺) Hz, 1H), 8.19-8.12 (m, 2H), 7.82-7.75 (m, 2H), 7.48 (dd, J =8.5, 2.3 Hz, 2H), 7.39 (d, J = 8.5 Hz, 2H), 7.31 (d, J = 8.0 Hz, 1H),7.24 (s, 1H), 6.85 (s, 1H), 5.15 (t, J = 6.7 Hz, 1H), 4.70-4.38 (m, 2H),4.05-3.91 (m, 2H), 2.55 (tt, J = 13.5, 6.8 Hz, 1H), 2.32 (d, J = 1.6 Hz,3H), 1.21-1.06 (m, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.02 A47 ESIMS m/z644 ¹H NMR (400 MHz, CDCl₃) δ 8.57 (d, J = 1.4 ([M + H]⁺) Hz, 1H),8.19-8.13 (m, 2H), 7.83-7.77 (m, 2H), 7.51-7.42 (m, 5H), 7.40 (d, J =8.6 Hz, 2H), 7.04 (dd, J = 7.7, 3.4 Hz, 1H), 5.15 (t, J = 7.0 Hz, 1H),4.69-4.40 (m, 2H), 4.05- 3.96 (m, 2H), 2.60 (dt, J = 10.6, 6.8 Hz, 1H),1.17 (ddd, J = 8.9, 6.8, 3.1 Hz, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.02A48 ESIMS m/z 678 ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺)8.17 (d, J = 8.1 Hz, 2H), 7.80 (d, J = 8.9 Hz, 2H), 7.52-7.46 (m, 2H),7.38 (dd, J = 13.8, 8.6 Hz, 4H), 7.07 (t, J = 2.1 Hz, 1H), 5.16 (t, J =6.9 Hz, 1H), 4.75-4.40 (m, 2H), 4.00 (d, J = 2.7 Hz, 2H), 2.56 (dt, J =12.7, 6.5 Hz, 1H), 1.23-1.02 (m, 6H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03A49 ESIMS m/z 668 ¹H NMR (400 MHz, CDCl₃) δ 8.56 (s, 1H), ([M + H]⁺)8.08 (td, J = 6.0, 2.9 Hz, 2H), 7.85-7.75 (m, 2H), 7.39 (d, J = 8.6 Hz,2H), 7.31-7.27 (m, 2H), 7.18 (d, J = 8.6 Hz, 1H), 6.97 (d, J = 7.2 Hz,1H), 6.89 (dd, J = 8.5, 4.1 Hz, 1H), 5.20- 5.02 (m, 1H), 4.29 (q, J =5.4 Hz, 1H), 3.92 (d, J = 2.1 Hz, 2H), 3.10 (tt, J = 13.7, 6.6 Hz, 1H),2.76 (dq, J = 13.6, 6.7 Hz, 1H), 2.31 (d, J = 6.3 Hz, 3H), 1.55 (m, 2H),1.30-1.09 (m, 6H), 0.95-0.76 (m, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03A50 ESIMS m/z 624 ¹H NMR (400 MHz, CDCl₃) δ 8.55 (d, J = 1.9 ([M + H]⁺)Hz, 1H), 8.07 (t, J = 8.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.46 (d, J = 4.2Hz, 2H), 7.39 (d, J = 8.6 Hz, 2H), 7.36-7.25 (m, 3H), 7.06 (dd, J =10.4, 7.9 Hz, 1H), 5.08 (qd, J = 6.2, 3.1 Hz, 1H), 4.06-3.91 (m, 2H),3.05 (ddd, J = 33.0, 13.5, 6.5 Hz, 1H), 2.85-2.72 (m, 1H), 2.63 (dp, J =13.5, 6.8 Hz, 1H), 1.33-1.07 (m, 9H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.02A51 ESIMS m/z 626 ¹H NMR (400 MHz, CDCl₃) δ 8.57 (s, 1H), ([M + H]⁺)8.00 (t, J = 7.1 Hz, 2H), 7.83-7.77 (m, 2H), 7.40 (d, J = 8.5 Hz, 3H),7.18-6.87 (m, 5H), 5.16 (q, J = 6.2 Hz, 1H), 3.99 (dt, J = 33.0, 7.9 Hz,2H), 3.83 (d, J = 5.8 Hz, 2H), 2.85- 2.66 (m, 2H), 1.32-1.13 (m, 6H);¹⁹F NMR (376 MHz, CDCl₃) δ −58.03 A52 ESIMS m/z 624 ¹H NMR (400 MHz,CDCl₃) δ 8.56 (s, 1H), ([M + H]⁺) 8.07 (dd, J = 8.1, 3.2 Hz, 2H),7.84-7.75 (m, 2H), 7.39 (d, J = 8.7 Hz, 2H), 7.33 (td, J = 7.6, 1.6 Hz,1H), 7.28-7.24 (m, 2H), 7.24- 7.13 (m, 2H), 5.09 (ddd, J = 11.6, 7.1,3.8 Hz, 1H), 3.97 (d, J = 1.7 Hz, 2H), 3.06 (ddd, J = 13.6, 9.6, 6.6 Hz,1H), 2.78 (ddd, J = 13.3, 7.0, 4.0 Hz, 1H), 2.41 (p, J = 7.4 Hz, 2H),2.12 (d, J = 2.0 Hz, 3H), 1.27 (t, J = 5.9 Hz, 3H), 1.17 (t, J = 7.6 Hz,3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.03 A53 ESIMS m/z 608 ¹H NMR (400MHz, CDCl₃) δ 8.55 (s, 1H), ([M + H]⁺) 8.10-8.04 (m, 2H), 7.83-7.75 (m,2H), 7.40-7.35 (m, 2H), 7.34-7.24 (m, 4H), 6.98 (s, 1H), 6.85 (d, J =4.8 Hz, 1H), 6.68 (d, J = 4.8 Hz, 1H), 4.35 (ddt, J = 38.0, 10.8, 7.6Hz, 2H), 3.03 (t, J = 7.5 Hz, 2H), 2.58 (p, J = 6.9 Hz, 1H), 2.34 (s,3H), 1.21 (d, J = 6.8 Hz, 3H), 1.10 (d, J = 6.9 Hz, 3H); ¹⁹F NMR (376MHz, CDCl₃) δ −58.03 A54 ESIMS m/z 626 ¹H NMR (400 MHz, CDCl₃) δ 8.57(s, 1H), ([M + H]⁺) 8.21-8.15 (m, 2H), 7.82-7.76 (m, 2H), 7.46-7.37 (m,4H), 7.34 (dd, J = 8.0, 3.2 Hz, 1H), 7.28 (s, 1H), 6.99 (d, J = 1.8 Hz,1H), 6.88 (dd, J = 4.7, 0.9 Hz, 1H), 6.71 (dd, J = 4.7, 1.7 Hz, 1H),5.78 (ddd, J = 48.9, 7.9, 3.5 Hz, 1H), 4.56-4.27 (m, 2H), 2.58 (td, J =6.9, 3.3 Hz, 1H), 2.35 (d, J = 3.5 Hz, 3H), 1.21 (dd, J = 6.8, 2.3 Hz,3H), 1.11 (dd, J = 6.9, 2.2 Hz, 3H); ¹⁹F NMR (376 MHz, CDCl₃) δ −58.02,−185.63, −186.28 A55 ESIMS m/z 622 ¹H NMR (400 MHz, CDCl₃) δ 8.55 (d, J= 3.1 ([M + H]⁺) Hz, 1H), 8.09-8.01 (m, 2H), 7.83-7.76 (m, 2H), 7.38 (d,J = 8.5 Hz, 2H), 7.33 (dd, J = 8.0, 5.1 Hz, 1H), 7.30-7.23 (m, 3H),7.05- 6.95 (m, 1H), 6.83 (dd, J = 4.8, 2.2 Hz, 1H), 6.66 (t, J = 5.1 Hz,1H), 5.09 (q, J = 6.5 Hz, 1H), 3.12 (ddd, J = 40.5, 13.4, 6.0 Hz, 1H),2.80-2.67 (m, 1H), 2.57 (dp, J = 13.8, 6.9 Hz, 1H), 2.34 (d, J = 7.5 Hz,3H), 1.30-1.16 (m, 6H), 1.09 (dd, J = 15.1, 6.9 Hz, 3H); ¹⁹F NMR (376MHz, CDCl₃) δ −58.03

Example: Bioassays Insecticidal Test for Beet Armyworm (Spodopteraexigua, LAPHEG) (“BAW”)

Bioassays on beet armyworm (BAW; Spodoptera exigua: Lepidoptera) areconducted using a 128-well diet tray assay. One to five second instarBAW larvae are placed in each well (3 mL) of the diet tray that had beenpreviously filled with 1 mL of artificial diet to which 50 μg/cm² of thetest compound (dissolved in 50 μL of 90:10 acetone-water mixture) hadbeen applied (to each of eight wells) and then allowed to dry. Trays arecovered with a clear self-adhesive cover, vented to allow gas exchange,and held at 25° C., 14:10 light-dark for five to seven days. Percentmortality is recorded for the larvae in each well; activity in the eightwells is then averaged. In the reporting of the results, the “BAW & CLRating Table” was used.

Insecticidal Test for Cabbage Looper (Trichloplusia ni, TRIPNI) (“CL”)

Bioassays on cabbage looper (CL; Trichloplusia ni: Lepidoptera) areconducted using a 128-well diet tray assay. One to five second instar CLlarvae are placed in each well (3 mL) of the diet tray that had beenpreviously filled with 1 mL of artificial diet to which 50 μg/cm² of thetest compound (dissolved in 50 μL of 90:10 acetone-water mixture) hadbeen applied (to each of eight wells) and then allowed to dry. Trays arecovered with a clear self-adhesive cover, vented to allow gas exchange,and held at 25° C., 14:10 light-dark for five to seven days. Percentmortality is recorded for the larvae in each well; activity in the eightwells is then averaged. In the reporting of the results, the “BAW & CLRating Table” was used.

Insecticidal Test for Yellow Fever Mosquito (Aedes aegypti, AEDSAE)(“YFM”)

Master plates containing 400 μg of a molecule dissolved in 100 μL ofdimethyl sulfoxide (DMSO) (equivalent to a 4000 ppm solution) are used.A master plate of assembled molecules contains 15 μL per well. To thisplate, 135 μL of a 90:10 water/acetone mixture is added to each well. Arobot (Biomek® NXP Laboratory Automation Workstation) is programmed todispense 15 μL aspirations from the master plate into an empty 96-wellshallow plate (“daughter” plate). There are 6 reps (“daughter” plates)created per master. The created “daughter” plates are then immediatelyinfested with YFM larvae.

The day before plates are to be treated, mosquito eggs are placed inMillipore water containing liver powder to begin hatching (4 g. into 400mL). After the “daughter” plates are created using the robot, they areinfested with 220 μL of the liver powder/larval mosquito mixture (about1 day-old larvae). After plates are infested with mosquito larvae, anon-evaporative lid is used to cover the plate to reduce drying. Platesare held at room temperature for 3 days prior to grading. After 3 days,each well is observed and scored based on mortality. In the reporting ofthe results, the “YFM Rating Table” was used.

BAW & CL Rating Table % Control (or Mortality) Rating 50-100 A More than0-Less than 50 B Not Tested C No activity noticed in this bioassay D

YFM Rating Table % Control (or Mortality) Rating 80-100 A More than0-Less than 80 B Not Tested C No activity noticed in this bioassay D

Cmpd No BAW CL YFM A1 A A C A2 A A A A3 D D C A4 A A C A5 B A A A6 A A AA7 B A A A8 A A A A9 A A A A10 D A A A11 B A A A12 A A A A13 A A A A14 AA A A15 A A A A16 A A A A17 A A A A18 D D D A19 A A B A20 A A C A21 A AC A22 A A C A23 A A C A24 A A C A25 A B C A26 A* B* C A27 A A C A28 A AC A29 A A C A30 A A C A31 A A C A32 D A C A33 D A C A34 A A C A35 A A CA36 A A C A37 D A C A38 D A C A39 A A C A40 A A C A41 A A C A42 B A CA43 A D C A44 A A C A45 A A C A46 A A C A47 A A C A48 A A C A49 A A CA50 A A C A51 A A C A52 A A C A53 A A C A54 A A C A55 A A C *tested at 5μg/cm²

We claim:
 1. A molecule having the structure of Formula A:

wherein: (A) Ar¹ is selected from (1) furanyl, phenyl, pyridazinyl,pyridyl, pyrimidinyl, thienyl, or (2) substituted furanyl, substitutedphenyl, substituted pyridazinyl, substituted pyridyl, substitutedpyrimidinyl, or substituted thienyl, wherein said substituted furanyl,substituted phenyl, substituted pyridazinyl, substituted pyridyl,substituted pyrimidinyl, and substituted thienyl have one or moresubstituents independently selected from H, F, Cl, Br, I, CN, OH, SH,NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), SS(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y), C(═O)C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃,or S(═O)_(n)NR^(x)R^(y), or (Het-1), wherein each alkyl, haloalkyl,cycloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkenyl, cycloalkenyl,haloalkenyl, alkynyl, phenyl, phenoxy, and (Het-1) substituent may beoptionally substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo,NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl,C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl),(C₁-C₈ alkyl)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁₋₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁₋₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)OC₁-C₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, phenoxy, Si(C₁-C₈ alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1); (B)Het is a 5- or 6-membered, saturated or unsaturated, heterocyclic ring,containing one or more heteroatoms independently selected from nitrogen,sulfur, or oxygen, and where Ar¹ and Ar² are not ortho to each other(but may be meta or para, such as, for a five-membered ring they are 1,3and for a 6-membered ring they are either 1,3 or 1,4) and where saidheterocyclic ring may also be substituted with one or more substituentsindependently selected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo,thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl),(C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃, orS(═O)_(n)NR^(x)R^(y), wherein each alkyl, haloalkyl, cycloalkyl,halocycloalkyl, alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl,alkynyl, phenyl, and phenoxy substituent may be optionally substitutedwith one or more substituents independently selected from H, F, Cl, Br,I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy,C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl,C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁₋₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁₋₈ alkyl), (C₁-C₈alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃,or S(═O)_(n)NR^(x)R^(y); (C) Ar² is selected from (1) furanyl, phenyl,pyridazinyl, pyridyl, pyrimidinyl, thienyl, or (2) substituted furanyl,substituted phenyl, substituted pyridazinyl, substituted pyridyl,substituted pyrimidinyl, or substituted thienyl, wherein saidsubstituted furanyl, substituted phenyl, substituted pyridazinyl,substituted pyridyl, substituted pyrimidinyl, and substituted thienyl,have one or more substituents independently selected from H, F, Cl, Br,I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy,C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl,C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl),C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl),C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1), wherein each alkyl,haloalkyl, cycloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkenyl,cycloalkenyl, haloalkenyl, alkynyl, phenyl, phenoxy, and (Het-1)substituent may be optionally substituted with one or more substituentsindependently selected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo,thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl),C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl),(C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁₋₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁₋₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, phenoxy, Si(C₁-C₈ alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1); (D)L is linker selected from (1) a bond, (2) —CR⁴R⁵—CR⁶R⁷—, or (3)—CR⁴═CR⁶—, wherein each of R⁴, R⁵, R⁶, and R⁷ is selected from H, F, Cl,Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈haloalkyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₃-C₈cycloalkenyl, C₃-C₈ halocycloalkenyl, C(═O)(C₁-C₆ alkyl), C(═O)O(C₁-C₆alkyl), C(═O)(C₃-C₆ cycloalkyl), C(═O)O(C₃-C₆ cycloalkyl), C(═O)(C₂-C₆alkenyl), C(═O)O(C₂-C₆ alkenyl), (C₁-C₆ alkyl)O(C₁-C₆ alkyl), (C₁-C₆alkyl)S(═O)_(n)(C₁-C₆ alkyl), C(═O)(C₁-C₆ alkyl)C(═O)O(C₁-C₆ alkyl),S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₁-C₈haloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), phenyl, or phenoxy; (E) R⁴and R⁶ together can optionally form a 3- to 7-membered saturated orunsaturated ring which may contain C═O, C═S, N, S or O, and isoptionally substituted with H, OH, F, Cl, Br, I, CN, NO₂, NR_(X)R^(y),C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ hydroxyalkyl, C₃-C₆ cycloalkyl,C₃-C₆ halocycloalkyl, C₃-C₆ hydroxycycloalkyl, C₃-C₆ cycloalkoxy, C₃-C₆halocycloalkoxy, C₃-C₆ hydroxycycloalkoxy, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, C₂-C₆ alkenyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkynyl, S(═O)_(n)(C₁-C₆ alkyl), S(═O)_(n)(C₁-C₆ haloalkyl),OSO₂(C₁-C₆ alkyl), OSO₂(C₁-C₆ haloalkyl), C(═O)H, C(═O)OH,C(═O)NR_(x)R_(y), (C₁-C₆ alkyl)NR_(x)R_(y), C(═O)(C₁-C₆ alkyl),C(═O)O(C₁-C₆ alkyl), C(═O)(C₁-C₆ haloalkyl), C(═O)O(C₁-C₆ haloalkyl),C(═O)(C₃-C₆ cycloalkyl), C(═O)O(C₃-C₆ cycloalkyl), C(═O)(C₂-C₆ alkenyl),C(═O)O(C₂-C₆ alkenyl), (C₁-C₆ alkyl)O(C₁-C₆ alkyl), (C₁-C₆alkyl)S(═O)_(n)(C₁-C₆ alkyl), C(═O)(C₁-C₆ alkyl)C(═O)O(C₁-C₆ alkyl),phenyl, phenoxy, and Het-1; (F) Q¹ is selected from O or S; (G) Q² isselected from O or S; (H) R¹ is selected from (J), H, C₁-C₈ alkyl, C₃-C₈cycloalkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, C(═O)(Het-1), (Het-1), (C₁-C₈alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-O—C(═O)O—(C₁-C₈ alkyl),(C₁-C₈ alkyl)-O—C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)-C(═O)N(R^(x))(C₁-C₈alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)(Het-1), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)OH, (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(x))(R^(y)), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)(N(R^(y))C(═O)O—(C₁-C₈ alkyl)C(═O)OH,(C₁-C₈ alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)O—(C₁₋₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁₋₈ alkyl), (C₁-C₈alkyl)-OC(═O)—(C₃-C₈ cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈alkyl)-OC(═O)—(C₁-C₈ alkyl)N(R^(x))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-NR^(x)R^(y), (C₁-C₈ alkyl)-S-(Het-1), (C₁-C₈alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1), wherein each alkyl,cycloalkyl, phenyl, and (Het-1) are optionally substituted with one ormore substituents independently selected from H, F, Cl, Br, I, CN, OH,SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)H, C(═O)OH, C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y), C(═O)(C₁-C₈alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl),C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, phenoxy, Si(C₁-C₈ alkyl)₃, S(═O)_(n)NR^(x)R^(y), or (Het-1); (I)R² is selected from (J), H, OH, SH, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)H, C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,C(═O)(Het-1), (Het-1), (C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)—(C₁-C₈alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-O—C(═O)O—(C₁₋₈alkyl), (C₁-C₈ alkyl)-O—C(═O)NR^(x)R^(y), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁₋₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)(Het-1),(C₁-C₈ alkyl)-C(═O)N(R^(x))(C₁₋₈ alkyl)N(R^(y))C(═O)OH, (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(x))(R^(y)), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)N(R^(y))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-C(═O)N(R^(x))(C₁-C₈ alkyl)(N(R^(y))C(═O)O—(C₁-C₈ alkyl)C(═O)OH,(C₁-C₈ alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈alkyl)-OC(═O)—(C₃-C₈ cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈alkyl)-OC(═O)—(C₁-C₈ alkyl)N(R^(x))C(═O)O—(C₁-C₈ alkyl), (C₁-C₈alkyl)-NR^(x)R^(y), (C₁—C alkyl)-S-(Het-1), (C₁-C₈alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1), wherein each alkyl,haloalkyl, cycloalkyl, halocycloalkyl, cycloalkoxy, halocycloalkoxy,alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl, alkynyl, phenyl,and (Het-1), are optionally substituted with one or more substituentsindependently selected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo,thioxo, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl,C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)OH, C(═O)(C₁-C₈alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl),C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, halophenyl, phenoxy, and (Het-1); (J) R¹ and R² may be a 1- to4-membered saturated or unsaturated, hydrocarbyl link, which may containone or more heteroatoms selected from nitrogen, sulfur, and oxygen, andtogether with (Q²)(C)(N) forms a 4- to 7-membered cyclic structure,wherein said hydrocarbyl link may optionally be substituted with one ormore substituents independently selected from H, F, Cl, Br, I, CN, OH,SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)H, C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁₋₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁₋₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, substituted phenyl, phenoxy, or (Het-1); (K) R³ is selected fromC₃-C₈ cycloalkyl, phenyl, (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,(C₂-C₈ alkenyl)-O-phenyl, (Het-1), (C₁-C₈ alkyl)-(Het-1), (C₁-C₈alkyl)-O-(Het-1), wherein the C₃-C₈ cycloalkyl, phenyl, (C₁-C₈alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, (C₂-C₈ alkenyl)-O-phenyl, (Het-1),(C₁-C₈ alkyl)-(Het-1), or (C₁-C₈ alkyl)-O-(Het-1) may be optionallysubstituted with one or more substituents independently selected from H,F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl,C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy,C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl,S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl),S(═O)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl),OSO₂(C₁-C₈ haloalkyl), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈haloalkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, phenoxy, Si(C₁-C₈ alkyl)₃,S(═O)_(n)NR^(x)R^(y), or (Het-1) or wherein two adjacent substituentsform a 5- or 6-membered saturated or unsaturated, hydrocarbyl link,which may contain one or more heteroatoms selected from nitrogen,sulfur, and oxygen, and wherein said hydrocarbyl link may optionally besubstituted with one or more substituents independently selected from H,F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆ alkyl),S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo; (L) R^(x) and R^(y) areindependently selected from H, OH, SH, C₁-C₈ alkyl, C₁-C₈ haloalkyl,C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)H, C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁₋₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁₋₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, C(═O)(Het-1),(Het-1), (C₁-C₈ alkyl)-(Het-1), (C₁-C₈ alkyl)-C(═O)—(C₁-C₈ alkyl),(C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-O—C(═O)O—(C₁-C₈alkyl), (C₁-C₈ alkyl)-C(═O)(Het-1), (C₁-C₈alkyl)-C(═O)(Het-1)C(═O)O—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)O—(C₁-C₈alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₁-C₈ alkyl), (C₁-C₈ alkyl)-OC(═O)—(C₃-C₈cycloalkyl), (C₁-C₈ alkyl)-OC(═O)-(Het-1), (C₁-C₈ alkyl)-S-(Het-1),(C₁-C₈ alkyl)S(═O)_(n)(Het-1), or (C₁-C₈ alkyl)-O-(Het-1), wherein eachalkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkoxy,halocycloalkoxy, alkoxy, haloalkoxy, alkenyl, cycloalkenyl, haloalkenyl,alkynyl, phenyl, and (Het-1), are optionally substituted with one ormore substituents independently selected from H, F, Cl, Br, I, CN, OH,SH, NO₂, oxo, thioxo, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)OH, C(═O)(C₁-C₈alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl),C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl,phenyl, halophenyl, phenoxy, and (Het-1), or R^(x) and R^(y) togethercan optionally form a 5- to 7-membered saturated or unsaturated cyclicgroup which may contain one or more heteroatoms selected from nitrogen,sulfur, and oxygen, and where said cyclic group may be substituted withH, F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, C₁-C₈ alkyl, C₁-C₈haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy,C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl,C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl),S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl),C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈ alkyl)phenyl, (C₁-C₈alkyl)-O-phenyl, phenyl, substituted phenyl, phenoxy, and (Het-1); (M)(Het-1) is a 5- or 6-membered, saturated or unsaturated, heterocyclicring, containing one or more heteroatoms independently selected fromnitrogen, sulfur or oxygen, wherein said heterocyclic ring may also besubstituted with one or more substituents independently selected from H,F, Cl, Br, I, CN, OH, SH, NO₂, oxo, thioxo, NR^(x)R^(y), C₁-C₈ alkyl,C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy,C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkynyl,S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈ halocycloalkyl),S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl), OSO₂(C₁-C₈ alkyl),OSO₂(C₁-C₈ haloalkyl), C(═O)NR^(x)R^(y), (C₁-C₈ alkyl)NR^(x)R^(y),C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ haloalkyl),C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈ cycloalkyl), C(═O)O(C₃-C₈cycloalkyl), C(═O)(C₂-C₈ alkenyl), C(═O)O(C₂-C₈ alkenyl), (C₁-C₈alkyl)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)O(C₁-C₈ haloalkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁₋₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl),(C₁-C₈ alkyl)C(═O)O(C₁-C₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl),(C₁-C₈ alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, and phenoxy,wherein each alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, phenyl, andphenoxy may be optionally substituted with one or more substituentsindependently selected from H, F, Cl, Br, I, CN, OH, SH, NO₂, oxo,thioxo, NR^(x)R^(y), C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₁-C₈alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyl, C₃-C₈ cycloalkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkynyl, S(═O)_(n)(C₃-C₈ cycloalkyl), S(═O)_(n)(C₃-C₈halocycloalkyl), S(═O)_(n)(C₁-C₈ alkyl), S(═O)_(n)(C₁-C₈ haloalkyl),OSO₂(C₁-C₈ alkyl), OSO₂(C₁-C₈ haloalkyl), C(═O)H, C(═O)NR^(x)R^(y),(C₁-C₈ alkyl)NR^(x)R^(y), C(═O)(C₁-C₈ alkyl), C(═O)O(C₁-C₈ alkyl),C(═O)(C₁-C₈ haloalkyl), C(═O)O(C₁-C₈ haloalkyl), C(═O)(C₃-C₈cycloalkyl), C(═O)O(C₃-C₈ cycloalkyl), C(═O)(C₂-C₈ alkenyl),C(═O)O(C₂-C₈ alkenyl), (C₁-C₈ alkyl)O(C₁-C₈ alkyl), (C₁-C₈alkyl)S(═O)_(n)(C₁-C₈ alkyl), (C₁-C₈ alkyl)OC(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)OC(═O)O(C₁-C₈ alkyl), C(═O)(C₁-C₈ alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈alkyl)C(═O)O(C₁₋₈ alkyl), (C₁-C₈ alkyl)C(═O)(C₁-C₈ alkyl), (C₁-C₈alkyl)phenyl, (C₁-C₈ alkyl)-O-phenyl, phenyl, and phenoxy; and (N) n iseach individually 0, 1, or
 2. 2. The molecule of claim 1, having thestructure of Formula One, Formula Two, or Formula Three:

wherein: (A) Ar¹ is a phenyl or substituted phenyl having one or moresubstituents independently selected from C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₁-C₆ alkoxy and C₁-C₆ haloalkoxy; (B) Het is triazolyl; (C) Ar² is aphenyl or a substituted phenyl having one or more substituentsindependently selected from F, Cl, Br, I, CN, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ alkoxy, and C₁-C₆ haloalkyl; (D) Each R⁴, R⁵, R⁶, and R⁷ isselected from a H, F, Cl, Br, I, CN, oxo, C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl,C₃-C₆ cycloalkenyl, C₃-C₆ halocycloalkyl, and phenyl; (E) R¹ is selectedfrom (J), H, C₁-C₆ alkyl or C₂-C₆ alkenyl, wherein said alkyl or alkenylis optionally substituted with a C₃-C₆ cycloalkyl or C₁-C₆ alkoxy; (F)R² is selected from (J), H, OH, SH, C₁-C₆ alkyl or C₂-C₆ alkenyl,wherein said alkyl or alkenyl is optionally substituted with a C₃-C₆cycloalkyl or C₁-C₆ alkoxy; (G) R³ is phenyl or (Het-1), wherein thephenyl or (Het-1) may be optionally substituted with one or moresubstituents independently selected from H, F, Cl, Br, I, CN, OH, SH,NO₂, NR^(x)R^(y), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, (C₁-C₆ alkyl)O(C₁-C₆alkyl), (C₁-C₈ alkyl)O(C₁-C₈ haloalkyl), (C₁-C₆ alkyl)S(═O)_(n)(C₁-C₆alkyl), C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆ alkyl),S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo or wherein two adjacentsubstituents form a 5- or 6-membered saturated or unsaturated,hydrocarbyl link, which may contain one or more heteroatoms selectedfrom nitrogen, sulfur, and oxygen, and wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆alkyl), and S(═O)_(n)(C₁-C₆ haloalkyl); (H) R^(x) and R^(y) areindependently selected from H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆cycloalkyl, C₃-C₆ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, andphenyl; (I) (Het-1) is a 5- or 6-membered, saturated or unsaturated,heterocyclic ring, containing one or more heteroatoms independentlyselected from nitrogen, sulfur or oxygen, wherein said heterocyclic ringmay also be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo; and (J) R¹ and R²may be a 1- to 4-membered saturated or unsaturated, hydrocarbyl link,which may contain one or more heteroatoms selected from nitrogen,sulfur, and oxygen, and together with (Q²)(C)(N) forms a 4- to7-membered cyclic structure, wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆alkyl), S(═O)_(n)(C₁-C₆ haloalkyl), phenyl, and oxo.
 3. The molecule ofclaim 1, wherein Ar¹ is a substituted phenyl having one or moresubstituents independently selected from OCF₃, OCF₂CF₃, and CF₃.
 4. Themolecule of claim 1, wherein Het is 1,2,4-triazolyl.
 5. The molecule ofclaim 1, wherein Ar² is a phenyl.
 6. The molecule of claim 1, whereinAr² is a substituted phenyl having one or more substituentsindependently selected from H, F, Cl, Br, I, CN, C₁-C₆ alkyl, and C₁-C₆alkoxy.
 7. The molecule of claim 1, wherein R¹ and R² together form a5-membered ring containing one or two C═O, and such ring is optionallysubstituted with H, OH, F, Cl, Br, I, CN, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, phenyl or phenoxy.
 8. The molecule ofclaim 1, wherein each of R⁴, R⁵, R⁶, and R⁷ is independently H, F, Cl,or a C₁-C₆ alkyl.
 9. The molecule of claim 1, wherein R³ is asubstituted phenyl with one or more H, F, Cl, Br, I, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₃-C₆ cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, (C₁-C₆alkyl)O(C₁-C₆ alkyl), C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, or wherein twoadjacent substituents form a 5- or 6-membered saturated or unsaturated,hydrocarbyl link, which may contain one or more heteroatoms selectedfrom nitrogen, sulfur, and oxygen, and wherein said hydrocarbyl link mayoptionally be substituted with one or more substituents independentlyselected from H, F, Cl, Br, I, CN, OH, SH, NO₂, NR^(x)R^(y), C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, S(═O)_(n)(C₁-C₆alkyl), and S(═O)_(n)(C₁-C₆ haloalkyl).
 10. The molecule of claim 1having a structure selected from compounds listed in Table 1 TABLE 1Structures for Compounds A1

A2

A3

A4

A5

A6

A7

A8

A9

A10

A11

A12

A13

A14

A15

A16

A17

A18

A19

A20

A21

A22

A23

A24

A25

A26

A27

A28

A29

A30

A31

A32

A33

A34

A35

A36

A37

A38

A39

A40

A41

A42

A43

A44

A45

A46

A47

A48

A49

A50

A51

A52

A53

A54

A55


11. A process to apply a molecule according to claim 1 comprising,applying a molecule according to claim 1, to an area to control a pest,in an amount sufficient to control such pest.
 12. A process according toclaim 11, wherein said pest is beet armyworm (BAW), cabbage looper (CL),or yellow fever mosquito (YFM).
 13. A molecule that is a pesticidallyacceptable acid addition salt, a salt derivative, a solvate, or an esterderivative, of a molecule according to claim
 1. 14. A molecule accordingto claim 1 wherein at least one H is ²H or at least one C is ¹⁴C.
 15. Acomposition comprising a molecule according to claim 1 and at least oneother compound having insecticidal, herbicidal, acaricidal, nematicidal,or fungicidal activity.
 16. A composition comprising a moleculeaccording to claim 1 and a seed.
 17. A process comprising applying amolecule according to claim 1 to a genetically modified plant, orgenetically-modified seed, which has been genetically modified toexpress one or more specialized traits.
 18. A process comprising: orallyadministering; or topically applying; a molecule according to claim 1,to a non-human animal, to control endoparasites, ectoparasites, or both.